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What to do for our 2021 Cheap Car Challenge?

With 2019 in the bag and 2020 dragging on like a bad double date, it is time for us to look forward to 2021, when we can pretend everything will be OK and back to normal and all the dead people will come back to life and we’ll have solved racism.

Yup. 2021 is going to be the best.

No pressure!

Since everything will be great, I think it is OK to speculate on our 2021 road trip. About every two years, two friends and I buy cheap cars and then semi-immediately drive them on an epic road trip. We’ve done the west coast, we’ve done overlanding, and we’ve done Canada.


Against all odds all thee cars have always made it and against all odds all three of us want to do it again. (Though it was touch and go there for a while after AlCan...)


This year we’re looking to change things up a bit...

Lessons learned

Buying close to home

For the last trip we bought cars locally and had them shipped to/ driven to the start point in Tacoma, Washington. The reason for this was complicated, but boiled down to thinking crossing the border would be much more straightforward in cars we had 100% legal paperwork for, which necessitated buying in our home states.


This part we sort of liked a lot. I’d always maintained that part of the magic of the first two trips was only having two days to buy the car, but in actual fact buying them over a larger period of time didn’t diminish the excitement or the rush. What it did allow is each of us to buy our cars at our own pace, in our own way. I, for one, got a list of potentials, visited them in order of interest, and bought the first one that was “good enough”. George went for the “look at literally everything that is available” route and had a lot of fun with that too. Taylor, on the other hand, only had a weekend to buy so he ended up buying the only car whose seller would call/text/email/smoke signal him back.

And we all enjoyed the hell out of the process.

And we ended up with titles and registration in our names, which made selling them at the end a lot more straightforward.


What we did not enjoy was keeping the cars secret from each other. It was a lot of work for very little reward.

Additionally, buying local enabled us to work on our cars a little more extensively than previous trips had allowed, which, in theory, allowed us some more confidence in each of our vehicles. Taylor ended up with two new CVs, I ended up with new shock mounts and a non-leaking turbo (lol), and George, tragically, ended up with all new brakes.


Did our cars still break down on the trip? Oh course!

Taylor ended up with a truly massive coolant leak, I (probably) had a clogged PCV causing oil to go... everywhere, and George’s car started leaking oil from pretty much every possible place.


And that is OK.

Selling close to home

Lastly, a thing we have not enjoyed from these trips is selling the cars at the end. None of us did on the first trip, mind you, but on the second George and Taylor had a lot of stress and heartache associated with getting rid of their beloved companions... and I just kept mine again. On the most recent Taylor and I got lucky and sold ours within hours, but George barely got rid of his by the deadline and at a substantial loss.


So for this next one we’re all thinking that if we can start and end within 1200 or so miles of our respective homes, that would go a long way to (A) getting awesome cars and (B) getting more of our money back in the end. (Or make it cheaper for me to keep my car haha)

2021 Speculations


Each of us has championed a couple different ideas for this trip, though we’re pretty sure we’re honed in on one area.


In the past we’ve pitched the Lincoln Highway, the East Coast, Route 66, Mexico, the Gulf Coast, the Great Lakes, Canada Route 1, and even Iceland.

Initially I was a big fan of driving the Appalachian trail and getting involved with some of the trappings of that. All three were interested in exploring doing a distillery tour through Tennessee and Kentucky. Taylor was a big fan or exploring the Smokey Mountains and the Blue Ridge Parkway.


But it seems like all three of us agree we know nothing of Montana, Wyoming, and the Dakotas to the extent that (what we’re calling) the “mid-North” sounds like it might be our target.

The reason the “mid-north” appeals to us is predominantly it is an area of the country none of us have ever been to.

Illustration for article titled What to do for our 2021 Cheap Car Challenge?
Illustration: Akio

Starting City

Assuming the mid-North route, the two most discussed starting cities are Salt Lake City or Denver, the former being a moderate 2-day drive for most of us and the latter being a somewhat hellish 1-day drive. Alternatively, all three of us expect to be in WFH positions during this trip, so we could take an extra week or two and buy the cars in the starting city.


In either case, Salt Lake City is somewhat fraught as a starting city because it was the ending city for the 2017 trip. Given that we “started what we finished” in 2019, essentially resuming the 2015 trip from where we left off, starting at the end point of the 2017 trip seems... fraught.

That said, if we’re buying local and driving the cars to the start point, we could realistically start wherever we felt like it, not being limited by the size of the car market. Picking a random medium/ small town might make more sense?



Car Pitches (so far)

George floated the idea of purchasing softroaders rather than actual offroaders to make the trip in. I’m not opposed, but I’ve also done that...


I’m actually in favor of meeting in Dallas (we’re all close), buying cars at auction, driving them home, taking two - four weeks to improve them, and then set off. We have plenty of dealer contacts to make the auction thing happen and I feel like changing the format a bit might be fun! Also might make it harder to end up with an oddball, but I feel like I’ll manage?

That’s really all I’ve got so far though...

Next steps?

Easy enough. We need to start doing feasibility analysis, mock routes/schedules, and mock budgets. These will tell us how far we can reasonably go in the time we have available. Usually after displaying a couple options we start to hone in on one or two and begin to refine them. Eventually a real route starts to develop from there.


Once we know where we’re going, we can take a stab at figuring out when. If I were to guess I’d say August 2021, but who can say.

Annnnnd... that’s all I’ve got.

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