However, it needs to be done correctly from the outset, I recommend using an attorney. 

Is that correct?  

The questions you are asking are far to vague for anyone to have major input or guide you correctly as each person's situation is different. 

I would like to make a correction, actually, they are in Foley, not in Gulf shores.

I believe everything is going to correct and we'll see losses in more than just STR.Buy property and do everything you can to hold onto it forever.

Also, most property managers dont actually do the lawn and snow, correct? 

If an experienced investor has more to add or can correct me if I am wrong can chime in. 

Ultimately you need to put in what the masses will like and not what you like.I do a lot of contemporary designed homes and some of them get white shaker cabinets while others get grey shaker or some other contemporary style and color.

While he should have been educating himself in real estate principles, finance and law, he was instead learning about weasel clauses, driving for dollars. and what color postcards to mail out. 

Unless the infraction is egregious impossible to correct, the first step is a lease violation warning.