I haven't really thought about that as I have never done any type of rehab work - So my intentions were to buy something in relatively good condition and rent it out right away.

Just remember, repairs of roof etc will be needed down the road unless in excellent condition.

They had explained that one member of the family had a diagnosed condition which would benefit from a service dog (sorry to be vague, but I'm not sure if saying the actual diagnosis is illegal).  

I think everything you mentioned @Chris Seveney about the risks with value, condition, borrower difficulties, and potential lien/title issues nailed it. 

While it’s a little messed up from a social perspective, gentrification (particularly younger folks) coming in usually means an area is turning, at least for a lot of the hot areas ITP.

It all depends on how much leverage is being used, what type and condition the properties are in, and what submarket of greater Orlando you are looking in, etc.

Would you say, get good property inspections, have MY property managers approve the current tenants and condition of the property, but generally move along? 

Allows landlord to terminate tenancy with 90 days’ written notice and payment of one month’s rent under certain conditions.

I then go on social media and try to find one of their relatives, then you can send them a personal message. 

Other than contacting former guests, posting on Craigslist and social media (which has only given me leads that don't turn into bookings), what should I do to help get these months booked up?