Hi Reader, Cities and town ordinances talk about what’s allowed for rentals. That’s now. People tell you what’s about to change. That’s your future. And by people I mean yes, the people who live there, with whom you can have a local conversation. But also, people's voices in the paper. And what’s on the town agenda. These are the leading indicators: these “conversations” let you know which direction the town is heading when it comes to different types of rentals, and that can have direct...
7 days ago • 3 min read
Hi Reader, If you're weighing a short-term rental, you've probably already found a projected income number. It may belong to someone else, though. Most of those numbers come off a spreadsheet built for a different house, under an ordinance written in the past, in a town that may have changed its mind since. Over 26 years, the rules where I've operated have been rewritten five times, and in one neighboring town an entire licensing system came down to two votes. So the real decision isn't...
15 days ago • 3 min read
Hi Reader, One neighbor, once, in twenty-six years, called the town instead of calling me when they had a concern. It was about a trash enclosure that was in the wrong spot, apparently, for the way the street liked to look. I hadn't given him any other option: no name, no number, so all he had was a street address to report. We moved the enclosure right away. Done. But the lesson wasn't about the enclosure. It was that the one time a neighbor skipped me and went straight to the town was the...
about 1 month ago • 2 min read
Hi Reader, A couple of weeks ago I made the case for mid-term rentals and wrapped up the piece saying that you can pivot when the season changes. Which is true. Reader comments reflected that sometimes what’s hard, though, is knowing which season you’re actually in. A pattern in short-term renting is that, around month six, owners find that they’re tired. The turnovers have added up, the 9pm messages have added up, and somewhere in there a suspicion sneaks up: what if I picked the wrong type...
3 months ago • 3 min read
Hi Reader, If you've spent three months reading about renting out your space and you're further from a decision than when you started, the research isn't the problem. The kind of research is. Every article you open adds a variable instead of subtracting one. So here's the assignment: spend one week as a field researcher on your own block. Not a week of deciding — a week of noticing. Open a note on your phone and log what you see for seven days. The signal I'd watch closest is how your...
3 months ago • 2 min read
Hi Reader, Most rental advice online assumes you want to squeeze every night. Drive the highest nightly rate, maximize occupancy, repeat. If you've got one property and a lifestyle you'd like to keep, that model may not be the best fit. There's one that straddles short-term and long-term rentals, and it's frequently overlooked. The essential question of fit A mid-term rental is a furnished lease that runs more than a month and less than a year – typically 3 to 6 months. It's long enough to...
3 months ago • 2 min read
Hi Reader, We can get distracted from our own rental optimization by others' glamor of theirs. Open Instagram and see owners optimizing, scaling, and posting their occupancy rates like box scores. Somewhere in that scroll a fear creeps in that you're behind. Behind what, though? You set the calendar for your property. No one else does. The deadline you're racing is one you invented, borrowed from people whose season looks nothing like yours. In nearly 30 years of doing this work, the owners...
3 months ago • 3 min read
Hi Reader, Years ago I stood in front of our guesthouse and could not decide whether to list it by the night, by the month, or by the season. I had the spreadsheet open. I had read everything. And I was completely stuck, because I was trying to answer the wrong question. I thought the question was, "How do I run a short-term rental well?" The real question was, "Is a short-term rental even the right model for this place, in this town, for the life I actually want?" Most people zip past that...
4 months ago • 2 min read