I live in a Winnebago now.

It all started in 2020, when I was faced with the tough decision of telling one of my housemates he needed to find a new place to live. I liked the guy and had zero complaints after six months of sharing a house with him, but he graded out as an overall “neutral” when it came to the house community contributions. I’ve been at this for a while now, and my ideal roommates aren’t just decent people who don’t cause trouble—I’m looking for people who bring something to the table. Specifically, I think that the ideal living situation for post-college unmarried guys is with other dudes who all buy into making each other better and have fun doing it. I want to have good conversations, be challenged, have overlapping social circles, and do things together (anything from having a house tv show, to going to see live music/improv, or just having a bonfire in the backyard). If you know me, you know I’m highly intentional in general and even more so when it comes to creating community, so this shouldn’t be a surprise. We become like the people we spend the most time around, so it’s important for these people to have qualities that qualify as “aspirational”, otherwise, we’ll stay stagnant or worse—drag each other down.

So, all the rooms in my house were full, but I had the opportunity to add a “plus” roommate, someone I knew wanted the same things I did. I changed my mind multiple times, and even went so far as to tell the prospective roommate to look elsewhere, but then I reneged. I truly empathized with the guy who was being replaced, but I am determined to be the type of person who can make tough decisions and have tough conversations in the pursuit of the best group outcome. Also, I am extremely wary of becoming complacent and settling for a decent existence when a better life is on the other side of discomfort. Change can be risky, but I was confident this would be a winning bet.

When I’m torn between two close choices, my mind is at its most creative. I try to look at the problem from every perspective, challenge every assumption, introduce random variables, and fully invest in imagining how these scenarios could turn out and how future-me feels about the possible outcomes, ex post facto. This is the first time I considered buying a trailer: “This guy just needs an affordable, safe place to sleep and nothing else—I could buy a trailer, park it in the backyard and rent it to him. All problems solved!” It was a good idea, but the timeline didn’t work (nor did my finances).

Fast forward to last spring, and the housing market in Austin was as crazy as any market I’ve seen or heard in my lifetime. Rents were rising, too, and right in the middle of this, one of my friends at work mentioned he was going to be looking for a place to live for the next school year. This got the gears turning in my head, even though I didn’t have any open rooms and the living situation had been great with the current guys (it was absolutely the right decision to make the switch, for those keeping score at home). I hadn’t really thought about the trailer thing in a while, as it would take a very specific type of person who would be willing to live in a trailer in that scenario. Definitely not something I would propose out of the blue to someone else looking for housing, and it would be risky to buy first then look for a fitting candidate. Dead end.

My entire life, up until five years ago when I bought my first house, my living situation included a shared bathroom. Life is much easier with an entire bathroom and walk-in closet to yourself, and I have fully appreciated the upgrade and never considered going back. So, when I first had the thought “I could be the one to live in the trailer”, I dismissed it immediately. I’m good, thanks. Not worth it.

The thought kept coming back, though. It has to be me. The fact my body (but my space! my bed! my stuff!) was so resistant initially actually became a selling point, as I started telling myself I was spoiled and complacent. I’ve trained myself to be suspicious of anything my body wants, and to habitually take things away just to prove I’m not addicted/reliant. It hasn’t quite gotten to the level of Ben Stiller’s “aversion therapy” techniques in Dodgeball, but sure, I’m well on my way! Comfort is the enemy of growth, and I’m all about learning new things and getting better via pushing my limits.

As I contemplated trailer life, block after block fell into place. It would be an adventure, and a great story. It would add an element of the unknown/excitement to the coming school year. It could build on the house community/dynamic. It could bring in more money (somewhat canceled out by the purchase of the trailer, but that gets complicated). It would be an experience that would test my endurance and allow me to learn things I would never be able to otherwise. I like all of those things! Besides, it’s not like I didn’t have a safety net—if anything went horribly wrong, I could end the experiment quickly.

Once I decided to go for it, I moved fast. I knew next-to-nothing about the local trailer market, but I immersed myself and picked it up quick. My first instinct was a self-contained RV, a “motorhome”. I learned about “Class A” (the big rigs), “Class B” (camper vans), and “Class C” (truck chassis). I learned that everyone wants a classic/retro Volkswagen pop-up camper van, to the degree most of what you pay for is the nostalgia and ability to post envy-worthy pictures on social media. I eliminated motorhomes from the search. That’s fine, this is part of why I bought an SUV in the first place—towing capacity adds options. My 2002 4Runner limited my towing options, though, as it’s rated for towing 5,000 lbs, the smallest group of “travel trailer” (aka conventional trailer). While I’m giving a lesson, additional options I never really considered included fifth-wheel (requires a truck bed) and pop-up trailers.. By the way, the Volkswagen comp of travel trailers are definitely Airstreams. If you think a shiny silver aerodynamic trailer perfectly fits your aesthetic, you’re not alone! [don’t worry, I’m basic in that regard, too—or I was]

So, these were the parameters I settled on:

• Travel trailer (towable)
• Under 5,000 pounds (the lighter the better)
• Local (I did not want to tow it farther than I had to)
• Bed separate from table (many tables in small trailers double as the bed—I didn’t want to have to switch back and forth)
• Either the lowest price point that got the job done (minimize cost), or barely used (maximize resale value)

I was also torn between taking out a loan to pay for it, compared to paying cash. This was an enormous dilemma, and I flip-flopped more times than I can count (I also considered a home equity line of credit, aka a HELOC). Ultimately, I based this decision on pure intuition. When my grandma, Mary John Wasson, died last September, she left me and my siblings Saving Bonds that she purchased back in the 1990’s. My grandma was a lifetime English teacher and librarian who lived her whole life in the town of Equality (population ~500). After her husband died in a car crash, leaving behind two young daughters (ages 4 and 2), she never remarried, and ended up supporting her own mother as well. [I will write a full post about her someday; she deserves it..] Somehow, even with all of this, she also owned one of the original Volkswagen camper vans, and she traveled the world, and she was financially-savvy enough to buy her grandkids savings bonds when they were only a couple years old! It just so happened that the current value of her gifted savings bond roughly equalled the trailer I decided to buy, and I figured there was nothing I could spend this money on that Grandma Mary would approve of more.

This is the trailer I ended up with: 2019 Winnebago Minnie Drop 170-S. Here is a fun video walkthrough, if you’re up for it: NEW!! MD170S Winnebago Minnie Drop (the world of trailer video reviews is as entertaining as you would expect). I got it for less than list price, and it was new enough that they still owed more money on their loan than I paid for it! Ultimately, the listing caught my eye when I first started looking, and I figured the bright red color and Winnebago brand name would pay off when I went to resell it (or, possibly rent it out by the night via RVshare.com or equivalent). In most cases, I would prefer to wait and get a better feel for the market over time, but I told myself I may never see another trailer like this for sale so close, so I just went for it. Within a week of that first thought (“I could live in an RV”), I had thought through the angles, done the research, made the offer, and I drove it home the next week. It felt risky yet calculated, which is my sweet spot.

Now that it was sitting in my driveway, I had a couple small problems to solve before my master plan could fall into place:

1. Find a new roommate & potentially reshuffle rooms.
2. Put in a gate wide enough to drive the trailer into my backyard.
3. Chop down several large trees that were potential hazards (they were killed in the winter storm).
4. Install a 30 amp outlet so I could plug into the house directly without causing problems.
5. Pack up, figure out what to do with my excess stuff, and move into the Winnebago!

Funny story: the first time I proposed this idea to the guy who initially sparked this idea, I had already made the offer on the trailer. So that was a ridiculous conversation, but I had so sold myself that I didn’t need him to say yes in order to follow through (he ended up declining joining our house, after much consideration). Getting the gate widened two feet was no problem for my handyman—he actually did it while I was out of town. The outlet was just as easy, though I tested a couple adapters before committing to the permanent solution. I love having a theme for my summers, so this summer turned out to be downsizing/minimalism. I read a couple books, found podcasts, watched the Marie Kondo series, and got rid of boxes and boxes and boxes of stuff. That has probably been the best part about all of this, honestly.. I’m super-sentimental and battle being a hoarder, and a ruthless culling was long overdue. The things I kept I sorted into trailer-worthy or stored in a shed in my backyard. One of my roommates works from home and has a dog, so it was an easy call to move him into the vacated master bedroom. By far the toughest part was finding a suitable roommate, but I was not about to rush the riskiest aspect, so I was patient, didn’t lower my standards, and the new arrangement has been working great so far (found him on Craigslist!). The only thing I have failed to do so far is get the trees chopped down, as it’s going to take professional equipment and there has been a backlog (ha).

I have tried to think of names for the trailer, and I haven’t quite found the right play on Winnebago/Winning/Wine/Winnie the Pooh/Whinny, but I have successfully overlooked the Matthew McConaughey-inspired innuendos. Speaking of which, there are two distinct reactions to my new living situation, and they are highly separated by gender. Guys tend to express jealousy they aren’t currently in a position to do something similar, and girls tend to express concern for my marriage prospects. Fine—there is a large middle group who just thinks I’m weird, but hey—that’s normal! Just over a month in, I’m loving the Winnebago life.