Anytime we’ve ever acquired a vacation rental property, it took so many successive miracles to pull off (finding a good deal, scraping together the downpayment, getting the loan, renovating and designing it, getting a cleaning crew, and then finally getting guests who love it).
Might be totally irrational, but I can’t imagine ever selling them after going through that process! They're like my little babies.
This great thread by @realEstateTrent made me rethink that this morning. Don’t know what the right answer is, but clearly a lot of wisdom here >>
Because these STRs aren’t really valued based on income, you’re not compensated adequately for improved operating performance if you ever sell. So, tough to execute a plan where improving the NOI leads to a big increase in asset value and sets you up for a big sale.
One day STRs might be valued based on income, but I’m not sure that will necessarily happen (many are so subscale, earnings are so variable based on property management). Or it might!
That said, anytime something remotely goes wrong at one of our homes, I suggest to my wife that maybe we should sell the place. She always tells me to get it together and just solve the problem 😂
So far she’s been right each time and anytime I considered selling it would have been a mistake. Some of the properties started to do way better than expected after holding on to them for a while. Or, the market for vacation homes just unexpected boomed driving up prices.
But a pretty fun business would probably be to fix up vacation homes and get them turnkey for renting out. Then you could rent them on your own or sell them to others. But we find these kind of properties so rarely, it would be a shame to ever part with them.

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More from @rohindhar

8 Dec
Our first guest that ever stayed at this property gave it 4 stars, which was a rough way to start. But since then it’s rattled off 67 five star reviews in a row😀
To be a "Superhost" on Airbnb, the main criteria is if you average a 4.8 star rating across your properties. So having a property that folks really really love can help you hit that average with a bit less stress.
The benefits of being a Superhost are kind of vague, but hopefully it helps you rank a bit better in the search results (or guests can book a new property with more confidence b/c it's a vetted host). Not sure whether it does anything or not!
Read 5 tweets
20 Oct
Since a lot of people asked me how does one exactly afford the downpayments for all these homes, I’d thought I’d break down roughly how my wife and I turned 1 house into 6.
(Note: this is somewhat simplified and not the exact timing of how things worked, but in retrospect, yes how things worked)
Started with house number 1. Paid 20% down plus modest renovation costs.
Read 9 tweets
19 Oct
These are the purchase prices of the homes in the small portfolio of vacation rentals owned by my wife and me.
All purchased with 20% down, mostly funded from the portfolio itself.
They’re all in different places (mostly to diversify risk, but also because that’s slightly more fun).
Read 5 tweets
7 Apr
There is a bit of a gold rush of people investing in Airbnbs and vacation rentals this year (related to pandemic remote work, interest rates, and perhaps the company’s IPO). I’m not sure if people realize quite how risky the asset class is.
This point was hit home the other day when listening to a podcast where someone with less than a year’s investing experience mentioned they were closing on 5 new Airbnb properties this month. Then i heard a podcast featuring someone with 5 properties and only 30 days experience!
So I thought I’d come up with a bunch of risks regarding investing in Airbnbs and vacation rentals.
Read 17 tweets
5 Feb
The most interesting thing we did during the pandemic was … we bought an Earthship! Image
An Earthship is an off-the-grid, self-sustaining home brilliantly designed by Michael Reynolds. It’s a house that half-buried in the earth, half greenhouse near Taos, New Mexico. en.wikipedia.org/wiki/Earthship….
The electricity source is solar. In the winter, it’s heated by the the south-facing greenhouse. It can be freezing outside, but this room gets very warm. Image
Read 13 tweets
4 Jan
New year, new project I wanted to share on Twitter!
My wife and I have started investing in vacation rental real estate (ie Airbnbs). First accidentally, then occasionally, now more seriously.
We bootstrapped a small portfolio of homes in Sonoma, Kauai, Taos, Mt. Hood. Started with about $150K in savings and have more than 10x that value in about 6 years. We’ve grown our starting investment around 70% a year after cashflow and appreciation.
Read 7 tweets

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