Every self-proclaimed real estate guru I knew told me I’d regret it.
We bought a short-term rental property near peak market in Florida. The HOA didn’t allow third-party management companies, so we had to owner operate it ourselves. Coordinating cleaners, managing bookings, fielding complaints from guests about things like the neighbor enjoying some time outside.
It felt like babysitting adults more than operating a business.
A few months in, we listed it. Sold within a few weeks at around a 40% ROI. The vacation rental market here was going off the charts, and we wanted out before it cooled down. The person who bought it from us has now been trying to sell it for over two years. So very glad we got out when we did.