This is a lot to take on from a distance and the chances of it going well are really, really low. 

Quote from @Juan Carlos Flores Garcia: Hi BP Community,I’m working on building a long-distance Section 8 rental portfolio, specifically in the Midwest with properties under $100K.

Looking to diversify my long term rental portfolio with some STRs in the Gulf Shores/Orange Beach area but I fully admit I'm short the knowledge in that space.

If you want something closer to home, the Poconos and Catskills are probably your best bets — both within easy weekend driving distance, with steady demand and a proven market for unique cabins.

I'm just starting out and looking to become a long-distance real estate investor.

How far, is too far, to self manage a SFH as a rental property? 2, 3, 4 hours?  

The city of Denver doesn't allow for non-owner occupied short-term rentals.

I stumbled upon this site while I was searching for ways to start a short-term rental business.

Hiring a full time Property Manager will likely make it difficult to execute the Short Term Rental Loophole, but many Property Managers offer consulting to allow you to fast track your learning curve on providing exceptional service.

@Isabel Cano reach out to @Josh Green if you are interested in running a successful short-term rental in the Tampa Bay area.