Call me a cynic, but in my experience a local saying “I’m just looking for a quiet weekend with my beau” can be translated directly to “I’m going to invite 30 people over, trash your house, and if all goes well the police will be called and you’ll have to pay your cleaners more than you earned on this booking.” 

Now, there are plenty of these types of properties ITP so you likely won't run into any issues unless you piss off the neighbors or ever have a county inspector come to the house for some reason.

@Nathan G. that is what I was thinking because she had plenty of time to get it back to me with whether or not she was going to vacate or renew with the rent increase and I even sent her a reminder and she said she would get the form back to me yesterday.

There’s plenty of RE gurus to read about, listen to and buy their stuff from.

There are plenty of other problems that can occur, so I avoid flood plains or even just properties in low lying areas (like at the bottom of a hill).

I'd agree I would certainly look outside of your immediate area - perhaps an adjacent market that's growing or has plenty of room to grow. 

You need to meet with them face to face, get plenty of references, look at one or two of their current projects, etc. 

Plenty of people overcome way more than what you're talking about, it shouldn't hold you back.....don't let it!

And don't worry, it's plenty expensive to find you a deal like that. ;)

Plenty of buyers for the smaller deals, too.