If you’re ever looking to invest in Florida, @Josh Green has a successful STR operations going on in the Tampa Bay Area that is providing his clients with solid returns year round.

Evaluate forming an LLC to protect both parties and outline everything in an operating agreement.

One thing I always remind people is it does not matter what is on a powerpoint presentation, the deal is dictated by whats in the PPM, operating agreement and subscription agreement. 

@Jay Hinrichs exactly the risk is even more than traditional development and the profit is actually less with more operational headaches.

I invest out of state in Pittsburgh from DC and self-manage everything, but it's taken me years to establish the right contacts, develop seamless processes etc. that allow me to handle everything remotely with confidence.

It also is helpful to have a California LLC in case you ever sell that property and move into another state so that you do not need to form a new LLC altogether with new operating agreement, just re-register in the new state as a new foreign LLC.

If your property management company is good and has built an internal maintenance team which has set rates and had strong relationship relationships with licensed contractor which should keep costs in control, you should never need to shop contractors on your own I wouldn't think.So in short, our policy is give us your preferred contractors upfront if you have them, but then we work all tickets to resolution including dispatch, and payment of invoices.This is of course for operational expenses.  

It sounds like you may be a better fit for a smaller operation that still offers guided tours.

We are familiar with several operators, but we chose to work with AJ Osborne at Cedar Creek Capital. 

And some expensive ones for larger operations.