We planned to retire in March of 2026, and from the beginning we knew we didn’t want retirement to arrive quietly. We wanted motion, an extended journey across the United States and Canada, following family ties and old roots. I still had family in Ontario; My wife Wendy had family in both Nova Scotia and Ontario. The map already felt personal before we ever unfolded it.
We live in rural western Kentucky, and by October of 2025 the idea of an RV stopped being a dream. If we were going to do this, we wanted time, time to learn the equipment, to make mistakes, to figure out what broke and how badly. And, just as important, we still had steady paychecks in case we needed to finance part of the dream.
Emails started arriving—sales pitches, “once-in-a-lifetime deals,” glossy photos of smiling retirees parked beside alpine lakes. The irony wasn’t lost on us: neither of us had ever set foot inside an RV. Not once.
Our first stop was a small RV dealer outside of Paducah. We wandered in one afternoon and got our first real introduction to the world we were about to enter. Most of what they sold were fifth wheels, the big rigs that hitch into the bed of a heavy-duty pickup. I was driving an F-150, and while I had faith in it, I also had limits. I was not looking to turn a retirement trip into dragging an entire house behind me.
My truck was only three years old and still smelled faintly new. In my mind, it was more than capable of handling the adventure ahead, within reason. That meant a fifth wheel was out, and one of our first nonnegotiable RV requirements became clear. Whatever we bought had to be something my trusty F-150 could realistically tow.
A week later we drove to Nashville, where a massive Camping World sprawled like an RV city. Rows and rows of rigs stretched out under the sky, each one promising some version of freedom. We walked the lot slowly, peering inside, opening doors, ducking our heads.
Wendy, of course, already had her requirements sorted. A king-size bed. A real kitchen. A shower and toilet that didn’t feel like an airline lavatory. And a lounge area where we could sit in the evening, eat dinner, and watch TV without feeling like we were camping inside a coffin.
The selection was dizzying. Enormous fifth wheels that felt more like condos. Bare-bones pull-behinds that were essentially a bed on wheels. And then the land yachts—motorhomes so large and luxurious they came with the psychological weight of a second mortgage.
We knew our limits. The pickup could comfortably tow around seven thousand pounds, which meant our options were already narrowing whether we liked it or not.
New RVs, old RVs. Big ones, small ones. No two were laid out the same. Wood frames versus aluminum frames. Composite siding versus metal. Slide-outs here, no slide-outs there. Every decision seemed to create three new variables. The combinations and permutations piled up fast, and before long the excitement gave way to a low-grade sense of overwhelm.
We hadn’t bought anything yet—but we were already learning that choosing an RV wasn’t just shopping. It was an education.
We wandered into the used section and that was where we found it. A Keystone Cougar. It had a twenty-two foot living area, with an overall length of twenty-six feet. It was considered a high-end model. Aluminum frame. Composite siding. One slide-out. Set up for winter camping. Three years old and in beautiful condition. It looked barely used.
It was also more expensive than most of the brand-new units we had just been through.
We walked through other rigs, opening cabinets, testing mattresses, nodding politely, but we kept drifting back to the Cougar. Once. Then again. Maybe a third time. Each visit lingered a little longer than the last.
Eventually I said it was time to go. I turned to Wendy and said, “Let’s get out of here.”
So we did. We walked to the truck, climbed in, and shut the doors.
Now, Wendy has a pattern when it comes to big purchases. I have seen it enough times to recognize the shape of it. It happened when we bought the tractor. We looked. We circled. We left. And just when I thought the decision was safely deferred, she would say something like, this looks like the one, or maybe we should just do it. The next thing I knew, we were back inside signing our life away.
I am not saying this is bad behavior. Over the years, that instinct has led us to some pretty great purchases. We tend to enable each other in good things and bad. That has worked out well more than once. Of course, it has also led us to buy some truly stupid things along the way.
That pattern showed up again here. And it would not be the last time that week.
We sat in the car for maybe thirty seconds before she said it. “We should go for it.”
So back in we went.
We bought the Keystone Cougar. An RV that was, if I am being honest, probably a little too big for our F-150.
Of course, we could not take it home that day. The unit still had to be prepped, whatever that meant . So we climbed back into the truck and headed home, waiting for the call that would tell us our new investment was ready.
The following week, after all the paperwork was signed and the insurance was in place and the RV was prepped, we went back to pick it up.
While we waited to pick up the unit, they tried to sell us start up kits, maintenance kits, and a plethora of other gadgets that we had no idea what they were for. Grey tank treatment, black tank treatment surge protectors, sewer hoses, water hoses. It was again overwhelming. It is hard to agree to buy a bunch of shit you have no idea what it is for and besides we had amazon. Anything they had we could get cheaper through the big A.
We did however purchase an anti-sway tow system for another thousand dollars. This was supposed to distribute the weight more evenly across the pickup to prevent swaying from a light front end. We both knew the pickup was probably on the small side for this RV, and this felt like the bare minimum required to pretend we were being responsible.
At the warehouse, a guy ran through all the features and maintenance of our new toy in about fifteen minutes. I absorbed maybe one minute of it. The rest vanished the moment he started talking faster than my brain could process.
Then we connected the F-150 to the new rig which looked like the Grinches small dog trying to pull Santa’s slay and we pulled out for the hour and a half drive home, towing our new behemoth.
If the anti sway kit did anything, it wasn’t obvious.
Th trip home was terrifying.
The front end of the truck felt like it was barely touching the ground. The steering went light and vague, and the whole rig wandered across the lane like it had opinions of its own. Fuel mileage immediately dropped from the twenty-two miles per gallon I normally got on the highway to nine. I could barely get the truck and trailer up to the speed limit, and we limped along I-24 at about sixty miles an hour.
Wendy sat glued to her phone looking down most of the way home. I asked what she was reading and she said, “Nothing. I am just trying not to witness the chaos around us or imagine the many creative ways this could end in a crash.” She kept scrolling as she said it, thumb moving steadily, eyes locked on the screen like it was a life raft. It was a deliberate act of denial, as if not looking might somehow change the laws of physics. Meanwhile, I was white knuckling the steering wheel, acutely aware that we were piloting several tons of truck and trailer down the interstate with optimism doing most of the work.
Finally, about halfway home, Wendy looked away from her phone, looked over at me and said, “You need a new truck.”
Lesson #1 – know the capacity of your truck or tow vehicle and ensure it is comfortably capable of towing your equipment.
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