Out of state AirBnB. Three birds, one stone?

[Phoebe Gavin]

Hello everyone,

I'm thinking about buying a vacation home on Sanibel Island, FL to solve few problems for myself. Just hoping to get your knee jerk reactions to the idea.

tl;dr: If I buy a 3 or 4-plex, let my broke retired parents live in it, and AirBnB the vacant units, would that be a net-positive or a net-negative for me?

All the details:

After the crash, my Dad's plumbing contracting business never really recovered. They'll be retiring in the next few years, but the funds will be pretty paltry. I'm toying with the idea of buying a multi-family home and letting them live in it rent-free in exchange for managing the AirBnB rental of the other units.

This would solve several problems for me:

• I wouldn't have to worry as much about their finances
• I'd have a nice place to stay when we visit
• We could build equity (albeit slowly) by paying off the off the property with the AirBnB income

My hunch is that this could work out just fine for everyone:

• My dad has been contracting for the last 35 years and is on the licensing board for the city of Sanibel. He could easily handle keeping rehab and repairs in check, as well as day-to-day maintenance.
• My mom cleans homes now and seems perfectly happy to do the between-guest cleaning
• My mom is a really tech savvy older person and could handle the online stuff involved with the Airbnb site, if I taught her
• We're incredibly close and I know I can trust them to take good care of my property
• My family is very well-connected on the island (First black family who ever lived there!) and finding good service providers for good prices would be easy for them.
• Sanibel is a tourist town with reliable year-round tourism. Nearly 100,000 tourists come through per year. 

I know that while my parents are living there rent-free, this isn't going to be a very profitable property. But I think if my goal is just to cover my expenses, while keeping them happy, active, and more financially secure - it's well worth sacrificing the cash flow from their unit. May as well get paid to help them rather than shell out, right?

What details have I failed to consider here? Do you think it's worth further exploration or is it just a nightmare waiting to happen?