Driven Through Time: My Journey with Cars

Occasionally, I find pleasure in embarking on a nostalgic expedition, reminiscing about my automotive journey throughout the years. Despite owning a multitude of vehicles, I cherish fond memories associated with each one. Join me on this captivating voyage, delving into the chronicles that originate before the acquisition of my driver’s license.

Acquired: Spring 2001
Model year: 1986
Model: Pontiac 6000 LE
Type: Sedan
Color: Blue

Technically, this was my first car, although I never had the chance to actually drive it on the road. My sister received a new hand-me-down vehicle, so she kindly passed this one down to me. At the time, I was still too young to legally drive, so the car remained parked in our yard for a year until it sadly succumbed to decay, rendering it unfit for the streets. I recall the bittersweet task of maneuvering the car within the yard, ensuring I could mow the grass beneath its stationary presence. Interestingly, it also held significance as my sister’s inaugural car, and I treasure memories of the two of us joyfully cruising around town once she obtained her driver’s license.

1986 Pontiac 6000
Not my actual car nor me pictured, but an accurate representation nonetheless

Acquired: Early 2003
Model Year: 1988
Model: Chevrolet Scottsdale 1500
Type: Pickup truck
Color: Red

Although not solely mine, this truck served as our family’s spare vehicle. Once I obtained my license in early 2003, I took up the exclusive responsibility of driving it to both work and school. However, on a frosty day during my commute to basketball practice, I encountered an untreated icy road. As I reached the peak of the road, the truck lost control, resulting in a distressing rollover into the nearby ditch. Regrettably, this incident marked the final time the truck was ever driven by anyone.

My actual truck and my good friend Zach posing with it

Acquired: Spring 2004
Model Year: 1990
Model: Chevrolet Cavalier
Type: Coupe
Color: White

Finally, I acquired my very first car, one that truly belonged to me and granted the freedom to go wherever and whenever I pleased. My great-grandfather, no longer capable of driving, offered me the opportunity to purchase his vehicle as I prepared to embark on my college journey. Acquiring the car for a mere $200, despite its rusting exterior and numerous repairs required, I wholeheartedly embraced the task of making it my own. Equipped with an MP3-CD player, an amplifier, and subwoofers, it transformed into the archetypal first car, a symbol of teenage independence.


Acquired: Summer 2005
Model Year: 1991
Model: Chrysler New Yorker Salon
Type: Sedan
Color: Silver

My trusty Cavalier, my reliable companion, unfortunately endured a fateful encounter with a deer that left it beyond repair. It became evident that it was time to bid farewell. However, as luck would have it, my sister once again received a new hand-me-down, resulting in me inheriting the second-hand hand-me-down, a silver Chrysler New Yorker that belonged to our grandmother. While undeniably a quintessential “grandma’s car,” I couldn’t care less because it boasted luxurious features like air conditioning, power locks, seats, and windows. I was riding in luxury!


Acquired: Fall 2006
Model Year: 1996
Model: Jeep Grand Cherokee Laredo
Type: SUV
Color: Silver

After patiently waiting, my older sister finally made the exciting leap to purchase her very own car, leaving me with the last remaining hand-me-down—a glorious Jeep that would become my first personal vehicle! This rugged beauty had the power to conquer any terrain and weather condition. I cherished every aspect of it, except perhaps the color. This versatile SUV served as the faithful steed that accompanied me on my journey towards independence, as I used it to move into my own apartment and embrace adulthood. It remained in my possession until 2013, when it transitioned into my third vehicle. Sadly, space constraints led me to part ways with it, and I managed to sell it for a steal at $1500, even by the standards of that time.


Acquired: Winter 2009
Model Year: 2004
Model: Chevrolet Trailblazer LS
Type: SUV
Color: Maroon

At the time, my future wife and I were sharing a living space, and the necessity for a second vehicle arose. Coincidentally, my uncle expressed his desire to part with his Trailblazer. I gladly embraced the opportunity, making it my daily driver. Similar to the Grand Cherokee, this resilient vehicle appeared capable of conquering any road conditions. However, it turned out to be the first vehicle that presented me with a plethora of issues. From faulty oxygen sensors to a troublesome transfer case, I found myself investing a significant amount of money to ensure its roadworthiness.


Acquired: Spring 2011
Model Year: 2008
Model: Chevrolet Trailblazer LT
Type: SUV
Color: Moondust

The initial experience with the Trailblazer did not deter me, as I promptly dove into another one, this time opting for a slightly newer model from a dealership. Determined to make a statement, I went all-in with modifications on this SUV, gradually transforming it into a stylish ride over the course of 2-3 years of ownership. The enhancements included a cutting-edge multimedia player with a video display, a convenient backup camera, an impressive amp and subwoofer setup, sleek 20-inch wheels, dazzling HID lights, and an intricate web of wiring to tie it all together.


Acquired: Summer 2012
Model Year: 2013
Model: Kia Optima SXZ
Type: Sedan
Color: Black

Following our marriage, my wife and I decided to embark on the exciting journey of purchasing our very first brand new car, which happened to be fully loaded with all the bells and whistles. Although our initial intention was to acquire an SUV or crossover, we ended up with a surprisingly powerful sedan that punched well above its weight for its time. It became the vehicle I affectionately dubbed my “first sports car.” We took this car on countless adventures, as it served as our daily drivers while we both commuted to the same office. However, the truth about our Kia soon became apparent. It required frequent visits to the dealership for repairs and maintenance, which fortunately were covered under warranty. Nevertheless, the countless hours spent dealing with these issues made us realize that our time was indeed precious and not easily replaced.


2013 – 2013 GMC Terrain SLE, SUV (Iridium)

Acquired: Winter 2013
Model Year: 2013
Model: GMC Terrain SLE
Type: SUV
Color: Iridium

Envious of the impressive features found in the Kia Optima, I made the decision to trade in my 2008 Trailblazer for what I believed was a promising SUV, the GMC Terrain. Initially drawn to its rugged aesthetic, my enthusiasm waned after a few months of driving, as it felt more akin to operating a minivan. Equipped with an underpowered 2.4L I-4 engine, the vehicle struggled to conquer the hilly terrain of Western Pennsylvania. It became evident that this purchase was a regrettable mistake, as keeping my Trailblazer would have likely been a wiser choice in the long run.


Acquired: Summer 2013
Model Year: 2013
Model: Ford Focust ST
Type: Hatchback
Color: Tangerine Scream

Feeling dissatisfied with the unenjoyable experience of driving the GMC Terrain, I yearned for something more thrilling. Despite having no prior experience with manual transmissions, I was enticed by the allure of mastering this skill, considering it the epitome of cool. What better way to learn than by purchasing a brand new car to practice on? Ironically, I couldn’t even drive it off the lot, requiring my dad to bring it home for me. Determined to become proficient, I dedicated numerous hours in the following days to learn the art of shifting gears, operating the clutch, and navigating the open road. Surprisingly, I picked up the techniques rather swiftly, and the rest, as they say, is history. However, my joy was short-lived, as after accumulating around 6,000 miles, I found myself involved in an accident that inflicted substantial damage upon my beloved Focus. While it should have been deemed a total loss, it miraculously survived. Unfortunately, the repairs took over three painstaking months, leaving me eagerly yearning to reclaim my rightful place behind the wheel.


Acquired: Summer 2014
Model Year: 2014
Model: Jepp Grand Cherokee Limited
Type: SUV
Color: Granite

Seeking to bid farewell to the Kia, my wife expressed her desire for a Jeep. Without conducting extensive research, we impulsively purchased one that appealed to our aesthetic preferences right off the lot. This marked our first experience with a leased vehicle, which seemed ideal considering our tendency to frequently switch cars. The Jeep, while fairly generic in its design, provided a smooth ride that we thoroughly enjoyed, and in our eyes, its appearance was quite impressive. It became our trusted companion during numerous memorable road trips. When the lease eventually expired, there was no doubt in our minds that we desired another Jeep to continue our automotive adventures.


Acquired: Winter 2016
Model Year: 2016
Model: Subaru WRX Limited
Type: Sedan
Color: Blue

A few years had passed since my accident with the Focus ST, and I felt it was time to move on from that chapter of my automotive journey. Aware that I would face significant financial losses due to the wreck and subsequent repairs, I accepted the inevitable hit on the trade-in value. After negotiating a deal, I took the leap and placed an order for a brand new Subaru WRX, equipped with a manual transmission, of course. The anticipation of driving off the lot in a faster and more exhilarating vehicle than my previous Focus heightened my excitement. True to my nature, I embarked on a journey of personalization, similar to what I did with my 2008 Trailblazer. The Subaru WRX underwent a series of modifications, including lighting enhancements, tinted windows, an upgraded exhaust system, and even a tuner to unleash its full potential. Undeniably, it was a thrilling car to drive, but I began to realize that it wasn’t the best fit for my body type, prompting me to seek a change and explore new automotive possibilities.


Acquired: Summer 2017
Model Year: 2018
Model: Jeep Grand Cherokee High Altitude
Type: SUV
Color: White

As we prepared to acquire a new Jeep, our hearts were set on finding one in a stunning white color with sleek black accents. Having come across a few similar models, we were resolute in our pursuit of this specific aesthetic. Out of all the Grand Cherokees we have owned, this one stood out as my personal favorite due to its striking appearance. One notable enhancement in this model year was the integration of Apple CarPlay, which, at the time, was a must-have feature for me. True to its predecessors and successors, this Jeep proved to be exceptional, consistently delivering reliable performance without ever letting us down.


Acquired: Spring 2014
Model Year: 2014
Model: Jeep Wrangler Unlimited Shara
Type: SUV
Color: Mojito!

Traditionally, I had regarded the Jeep Wrangler as an unattractive vehicle. However, the allure of a convertible SUV capable of venturing off-road intrigued me. When the JL model was announced, its new styling instantly captivated my attention, particularly in one of the newly introduced colors—green. Acquiring this specific shade proved to be a bit of a wait, as the Mojito! color wasn’t scheduled for production until Q2 of 2018. Although I had engaged with my Jeep dealer early on in 2018, it wasn’t possible to place an order just yet. As soon as the order banks opened for the coveted green Jeep, I eagerly arrived at the dealership, unbeknownst to them that the system was ready to accept my order. Naturally, I ordered a manual transmission.

Several months later, I bid farewell to my WRX as I traded it in for a brand new, four-door Jeep Wrangler. Owning this vehicle proved to be an immensely enjoyable experience. I found myself frequently switching between the hard and soft tops, and during summer, I relished the freedom of removing the doors. Adding my personal touch, as I had done with previous vehicles, I incorporated custom elements such as an exhaust system, a light bar, reverse lights, and even some homemade decals.

However, in 2022, I made the decision to bid farewell to the Wrangler. As it aged and ventured out of warranty, I recognized that the used car market was flourishing, presenting an opportune moment to secure a favorable deal. Consequently, I couldn’t resist parting ways with the Wrangler and seizing the advantageous offer that presented itself.


Acquired: Winter 2021
Model Year: 2021
Model: Jeep Grand Cherokee High Altitude
Type: SUV
Color: Black

Once again, it was time for a new Jeep Grand Cherokee, following the familiar pattern. This time, we opted for a sleek all-black paint with a stylish accent mix. Seeking an extra boost of power, we upgraded to the V8 Hemi engine. Presently, we continue to drive this vehicle, but we are actively searching for its successor. As of now, we are entertaining the possibility of straying from Jeep for the first time in quite a while. The outcome remains uncertain. While this particular Jeep Grand Cherokee has served us well overall, its technology and drivetrain have become outdated and are in need of a refresh.


Acquired: Spring 2021
Model Year: 2020
Model: Honda Grom 125
Type: Motorcycle
Color: Green

Driven by the desire to learn how to ride a motorcycle, I faced resistance from my concerned wife who believed it was too dangerous. To find a middle ground, we reached a compromise: I would opt for a small and slow bike that I could comfortably ride around town. This led me to the Honda Grom, and naturally, I chose it in a vibrant shade of green. With its 125cc engine, it struggles a bit to carry my larger frame, but it gets the job done. After the purchase, I enrolled in a motorcycle safety course and successfully obtained my license. As life has evolved with the arrival of our child and less available riding time, I find myself considering parting ways with the Grom. However, I genuinely enjoy the experience of riding a motorcycle, so we’ll see if I can persuade my wife to let me upgrade to something slightly larger and more suited to my current needs.


Acquired: Spring 2022
Model Year: 2022
Model: Toyota Tundra Platinum
Type: Pickup Truck
Color: Gray

Since I first started driving, I had always yearned for a pickup truck to call my own. Seeing most people around me with their trucks while I drove cars or less impressive SUVs intensified my desire. The primary obstacle that stood in my way was the price tag. As much as I longed for a top-of-the-line trim, it consistently exceeded my budget. However, when the announcement of the F-150 Lightning came, it felt like the perfect truck for me. Not only did it possess a bed and a frunk for storage, but it was also an electric vehicle—an appealing combination. Without knowing the precise pricing details, I eagerly placed a $100 deposit to secure a future opportunity to purchase one.

When the time finally arrived and the time slots and pricing were disclosed, it became apparent that the truck I desired was beyond my financial reach and would not be available for a couple more years. Determined to make my truck ownership dream a reality, I thoroughly explored every available truck option in early 2022. After careful consideration, I ultimately settled on the Toyota Tundra Platinum. The decision was influenced by various factors, including its technology features, and the offer I received for my Jeep Wrangler provided the means to step up to a new tier of vehicles. I joined a waiting list and patiently waited for about a month until I received a call informing me that the exact truck I desired was ready for delivery. Without even test driving it, I sold my Jeep to Driveway.com and, just a few days later, made the purchase of my truck.

Thus far, owning a truck has surpassed my expectations. I find myself utilizing it as a true workhorse more frequently than anticipated. Without hesitation, I can confidently say that I would happily buy another Tundra in the future.


What’s next?

I am already contemplating the replacement of my current Toyota Tundra with a newer model, as it offers upgraded features that were not available when I made my purchase. While the actual decision remains uncertain, if everything aligns, it may happen in 2024.

Meanwhile, the lease on our current Grand Cherokee is nearing its end, prompting us to actively search for the next vehicle. Presently, we have narrowed down our options to a shortlist that includes the 2024 Volkswagen Atlas Cross Sport, the 2024 Chevrolet Traverse RS, and, of course, the 2024 Jeep Grand Cherokee. Stay tuned to discover which of these options we will ultimately drive away with as our next vehicle!

Please enjoy this gallery of my car photography over the years:

I Sold My Car to Driveway.com

Spoiler: They picked it up in my driveway!

The used car market is at an all-time high and I did what any American would do and tried to take advantage of it. My daily driver has been a 2018 Jeep Wrangler (4-door) for the last 46 months. While I always like to shop around for my next vehicle, there hasn’t been much I was excited about. I usually keep my vehicles for two to three years before I get bored and trade them in on the new hotness. This Jeep has been an exception and might be the longest I’ve ever driven one continuous vehicle. Selling to Driveway wasn’t my first choice, but they were the highest bidder.

I made a YouTube video on the top 10 reasons why I’m selling my Wrangler.

You’ve probably seen all the online companies emerging that want to buy your car and pick it up for you. The popular ones being Carvana, Vroom, and Carmax, but I decided I was going to get prices from all of them. It’s an easy process to get a quote on selling your car. You just give them information about it and they give you a price instantly. Most of the time they honor that initial price throughout the buying process.

Last year I saw the announcement of the Ford F-150 Lightning, all electric pickup truck, and I was immediately enthralled with an electric truck. Ford took “pre-orders” of the Lightning models only to announce later that they wouldn’t be able to make that many quickly. Recently this year, Ford let me know that I won’t be getting a Lightning in the next 12 months. While sad about that, I was excited by the thought of having a truck, so I started looking at my options. All the while I was keeping an eye on what the value of my Jeep was. I never thought that I would sell it to a 3rd-party, but more likely would trade it to a dealer on a new car/truck.

In February of this year I told myself my next vehicle was going to be a truck, so I decided to actually keep tabs on my Wrangler price. Since then, the prices haven’t changed much, but I was pretty much going with the highest bidder. I found the prices to be all over the place and didn’t expect Driveway to be the leader. When I got quotes from each of these vendors I used the same information and options to make it fair across the board. I also used fake contact information because I didn’t want bothered and just wanted to see the price.

ServicePrice
Driveway$40,477
Carmax$38,500
WeBuyAnyCar$37,045
KelleyBlueBook$35,550
Carvana$33,280
Vroom$32,479
CarBrain$26,730
Peddle$18,745
My price tracking from the nine services I contacted
driveway promo image
Promo image from Driveway.com showing how easy it is to hand someone your keys

You can see how close the big names are, but hilariously CarBrain and Peddle are very low and not sure who would actually take that price. In my research I also learned about all the different companies that will offer to buy your car. Prior to this I didn’t know Carmax and KBB did the online buying thing. Additionally I also learned about services I’ve never heard of like CarBrain and Peddle.
There are some out there that I didn’t bother looking at mainly because they didn’t offer instant quotes online without talking to someone. My time is worth more than what you’re probably going to offer me. Initially I thought Vroom or Carvana would be one of the companies buying the Jeep, but Driveway surprised me.

I recently got word that my truck of choice was on it’s way from the factory to a dealer near me. This meant it was ‘go-time’ for me to sell the Wrangler to Driveway. I went through the online quote process with my real information and somehow it was lower (by $1,000) than the previous number I had. This was fine so I completed all the additional information requested. Shortly after, I was texted by a person from Driveway confirming details. Here’s where it starts to get shaky… this is the timeline of what happened next.

Thursday March 31stText conversation from John at Driveway: “Hello Ben, this is John from Driveway.com. I’m reaching out regarding your 2018 Jeep All-New Wrangler. We sent you an offer of $40,477. Are you interested in moving forward with selling that vehicle?” Why yes John, I am. “Can I call you to explain the process?”
Over an hour later John called me and talked me through what would happen next. I had made an appointment online for the next week to meet someone at a dealer near me to inspect the vehicle. Then they would schedule a date to come pick it up later. I asked a few questions about logistics and timing because I didn’t yet have a replacement vehicle. He assured me they were backed up and it would be 1-2 weeks before they came to get it.

“So… the person we had scheduled to pick up your Jeep next week can’t drive a stick shift”

Friday April 1st – Phone call from Jamie at Driveway: “We need to get approval from you, for your bank to release the payoff information on your car loan.” I was on the phone with Jamie for a while before we concluded that the bank might be closed for the day so we’d try again next week. Jamie also informed me that it might be too soon for them to get me a check for next week’s appointment. This is when I found out that the “inspection” appointment I made was the pickup my vehicle and take it away, appointment. I told her this was too soon and I needed to reschedule. So she was able to get my appointment rescheduled for the week after next.

Monday April 4th – Phone call from Susan at Driveway: “So… the person we had scheduled to pickup your Jeep next week can’t drive a stick shift, so we need to schedule someone who can drive a stick shift.” Susan even made me chuckle by calling it a “millennial anti-theft device” and I agreed, even though I’m a millennial.

Tuesday April 5th – Phone call from Susan again: We rescheduled the pickup and I had some more questions answered, because at this point basically everything changed. We scheduled the pickup on Monday April 11th and instead of it being at a nearby dealer, it was at my house. I told her that previously I thought it was somewhere else and she didn’t have record of that same information. No big deal, home is better for me. I asked about the payoff information and she said it looked good. She told me that they would provide me a check on Monday with the difference between the purchase price and my loan payoff, even though I thought I was getting a wire transfer. I also asked her to confirm the price. Susan said they had a lower price than my initial offer, but she was able to see that John mentioned the higher one, so they were going to honor that.

Tuesday April 5th – Phone call from Susan again: “Hi Ben, I have the bank on the line to confirm your information.” I talked to a representative from the bank I financed the Jeep through and confirmed everything. So now maybe we were actually ready and set for Monday.

Sunday April 10th – I received a reminder email from Driveway about my appointment on Monday. This was the first time I had an official appointment notice for the updated day/time. It was nice to know it was still happening. The email stated I needed to have my driver’s license, registration, keys, and all persons named on the title/registration needed to be present. Luckily that’s all me so I was ready.

I did some last minute gathering of all my personal belongings and left a few presents behind for the next owner. I didn’t bother cleaning the interior or exterior of the Jeep. I learned a long time ago that spending your own personal time cleaning a vehicle for trade/sell doesn’t actually return any additional value. I also left all my stickers/decals on the exterior. They can remove those.

I learned a long time ago that spending your own personal time cleaning a vehicle for trade/sell doesn’t actually return any additional value.

Monday April 11th – I got a call around 10am from Brian at Driveway. He was confirming some details and times. I told him I was able to meet earlier and so we planned for 11am. Shortly after 11, he arrived via Uber and greeted me.

The entire process took less than 15 minutes. He started the car, took some photos, looked around, and then gave me the check. He opted not to do a test drive since he was happy with what he saw. I had to sign some power of attorney documents (standard for vehicle sell/trade) and the sales documents. He removed my license plate and attached a dealer plate, then drove it away.

That deal is now done. They’re going to payoff the remainder of my loan and deal with my bank directly. The check I received is a difference between the sale amount and the payoff.

I had a lot of hesitation going into this process as I’ve never sold a car to anyone but a local buyer or dealer. Selling your car to an online service can be scary, but Driveway made it mostly easy the entire time. There were a few hiccups of scheduling, pricing, and information, but in the end it worked out. I can honestly say I would do this again tomorrow if I needed to. The only thing I lost in the deal was the tax benefit of trading in the Jeep at the same time of buying a new vehicle. The tax savings was about half of the difference Driveway offered, so still worth it to me.

Introducing: Double B Garage