The Old Broke Rancher on Starting a New Vacation Rental

By Gary Shelton | March 16, 2026

I recently heard of something called passive income from something called "Tik Tok." Passive income, it seems, is money that makes itself without you having to do anything. This struck me as an interesting and, indeed, attractive idea. As I look back over my seven or so decades alive on this earth, I don't think I ever made any passive income. What I did was I made toiling income. Drudging income. Work yourself down to a nub income. I did a lot of it. Which is to say, I did a lot of the working, but I didn't get all that much of the income. I'm guessing that you, dear reader, also know a little something about that.

So I got to thinking—maybe I should explore some of this passive income. But what would be my grift, er, my business? Why vacation rentals, of course! No doubt you've stayed at a few in your travels. All of America, it seems, is making money off of their extra space, putting up strangers in our homes and on our property. And when we're not doing that, we're the ones paying a premium to stay in someone else's extra room. I'm sure that this is true anywhere, but it seems to be especially true here in Montana, where there's always a mountain or river or badlands or prairie to explore. VRBO, Airbnb and so forth—we have become a nation of hoteliers.

The problem in my case is that my little house has absolutely no extra room. There's the kitchen, the bedroom where my wife and I sleep, our sons' rooms, the TV room, the mud room, the second TV room, a couple of bathrooms, and the pantry. All of which are currently occupied.

Okay, that meant I would need a brand-new building in which to house my vacation rental. I drove to the hardware store and, after some deliberation, settled on the Heartland Coronado, a 12 ft x 8 ft. gable-style wood shed with a window and a door. It was available with or without a floor, but I had imagined mine to be a sort of high-luxury plush Airbnb, so I opted for the floor option, loaded it onto my truck, and drove back to the ranch.

For an outbuilding with an interior encompassing a luxurious 96 sq. ft., it was remarkably difficult to assemble, requiring a second trip back to the hardware store for shingles, paint, roofing felt, caulk, and nails. Then I went inside the house and into the basement to search for furniture my wife wouldn't notice was absent. I came back up with a broken office chair, a bean bag chair abandoned by my children a half-decade back, and an inflatable mattress patched here and there by the judicious application of duct tape.

Once set up, I sat back to admire my work. Beautiful. Nevertheless, it was still missing something essential. I thought back on all the Airbnbs I had visited, trying to suss out what my little rental needed. Finally, I realized what it was. I ran inside the house, grabbed a sharpie and a piece of 8.5 by 11 office paper, wrote "Live, Laugh, Love" on it and tacked it to the wall of the shed.

The ambiance having been perfected, I knew there are certain things that a vacation rental needs, legally speaking. One of them is a place to answer nature's call. At first, I thought that the prospective guest already has the best bathroom in the world—one that is thousands of miles across and easy to ventilate: the great outdoors. But a cursory googling revealed that this will not be adequate, and so some sort of more official commode would have to be provided. To that end, I grabbed a spare porta-potty that I have on my property and bolted it to the side of the outbuilding.

As for licensing and permitting, I decided that as long as I was upfront about it, it wouldn't be a problem. I could just include it in the title, like "BEAUTIFUL, SPACIOUS SUITE OVERLOOKING MONTANA WILDS WITH ATTACHED BATHROOM SUITE. UNLICENSED".

Next I would need a listing, so I looked at some of the other high-class vacation rentals in the state and tried my best to replicate what made them so alluring. Here, for you to judge, is my effort:

"Nestled in the ample bosom of the Bear Paw mountains, under the watchful eye of our three rescue chihuahuas, lies an authentic Western retreat sitting on one of the most beguiling areas of our property. Here, a mere 215 miles from Glacier and only a brisk 340-mile drive to Yellowstone National Park, is the perfect place to find yourself, refresh your spirit, and take in the unparalleled views of our cattle pen and watering tanks as well as the vast majesty of the, uh, American tapestry. Amenities include a tasteful selection of art, breathtakingly comfortable bean bag chair, mattress that feels like sleeping on a nylon bag full of air, and a stylish rolling chair to convey you around the room in style. Life can be a beautiful dream when you stay at North Central Montana's most rusticly luxurious environs".

So I took some artfully blurry photos and affixed them to the profile and put it online. Now if that doesn't get people staying, I thought, I don't know what will.

Well, it wasn't long before I got an email from Airbnb and another from VRBO. Phrases like "not legitimate sleeping quarters" and "fraudulent listing," unkind and pernicious words like "violation of terms of service" and "permanently deactivated" were repeated in both.

Fine, I thought. I'll find some recent start-up, a precocious newcomer to the vacation rental world, and list it on there. I found one called "SECRETHIDEOUT.COM," which offers "no questions asked check in" and "cash only, no ID required" stays. My little rental unit has done surprisingly well on that website. And while the sullen, sunglasses-wearing men who arrive to stay in Chez OBR seem like nice enough guys, mostly sticking to themselves and moving nondescript bags in and out, I am beginning to think that this is not quite the class of person who I was trying to attract.

So I was going to try one more effort to make the place the passive-income-cash cow I was sure it could be, and to secure a finer sort of clientele; I was going to go inside, grab that Sharpie and another sheet of paper, and write out a whole series of new life-affirming, positive and even impishly funny phrases to put up on the walls. I'm talking the really good stuff, too, like "I'd Rather Be in the Mountains," "Memories are Made Here," and "But First, Coffee". If that doesn't work, I'll employ the nuclear option: "It's Wine O'Clock Somewhere".