I’m 29 and work in a pretty high-level sales job. I’ve been saving and investing since I was young, and recently bought my third property.
It is a waterfront, Gulf-access pool home in SWFL. I grew up around the previous owners and was able to get a really good deal on it. I put a lot of money and work into renovating it, and decided to turn it into an Airbnb.
A few months in, and the numbers haven’t been amazing.
I knew going into it that STRs aren’t just going to print money, and we’re also in one of the slowest periods for Florida. But I’m realizing how much of the carrying costs, utilities, cleaning, maintenance, supplies, repairs, platform fees, etc. (which is my fault for not running better numbers)
I’ve also found myself way more involved than I expected. I’m constantly trying to save money somewhere, fix something myself, coordinate things, improve the property, etc. My other investment property is a long-term rental duplex, and compared to this thing, the duplex feels like the greatest investment on earth.
What makes me think is, I have multiple realtor friends telling me that if I sold this property right now, I could realistically walk away with around $60k after commissions and closing costs. (They would be listing at a flat fee so they’re not just telling me this to make themselves money)
Part of me thinks, $60k in roughly 3 months isn’t exactly a bad outcome. Take the win, free up the capital, and move it into something else.
But then I remember something one of the people that inspired me to invest in real estate told me years ago that has always stuck with me. They said their biggest regrets were selling properties instead of turning them into rentals which makes me double guess.
Let’s say the Airbnb eventually becomes a high performer. Maybe I clear $20k/year after everything. Is that worth the additional wear and tear, management, headaches, and capital tied up in the property? Or would I be better off taking the $60k now and reinvesting it somewhere with better returns and less involvement?
The other issue is that I do love the property. I got a great deal and it’s the type of house I’ve always dreamt about owning. So there is a slight emotional attachment. But I’m trying really hard to separate “I love this house” from “is this is a good investment.”
So I guess I’m looking for opinions from people who have actually owned STRs or faced a similar decision.
Would you:
Stick it out for another year and see what the property does through a full cycle?
Sell now, take the \~$60k profit, and redeploy the money?
Consider converting it to a long-term rental?
Or am I looking at this completely wrong?
And no, I’m not a nepo baby, my parents aren’t rich, and nobody bought these properties for me lol. I’ve just been aggressive about saving and investing since I was young.
Interested to hear from people who have been in the game longer than me and can tell me whether I’m being impatient or whether taking a quick win is sometimes the smarter move.
I have about $100K of my own money tied up into the investment.