Other property owners have been running specials on rent to fill the vacancies, charging the same rent of $1200 that he signed a lease with us for the 2/2.

In Florida, we have to contact the property appraiser to determine unit numbers, because that is what the sheriff's office looks at when they execute a writ of possession to remove a tenant in an eviction. 

If the properties are decent I would find a realtor that specializes in investment sales and properly marekets them.

@Priscilla Z. has hosted an experience group in the past that specializes on wholesaling…I hope she responds for a time and place.CFRI Central Florida is the larger group, with classes offered.

The HOA funds are limited and if something happens, there will likely be a special assessment; roof and/or exterior paint are the big ticket items that are near end of life according to building assessment. 

I was hoping there maybe some special portfolio loan that may work but I may get a cosigner if all else fails.

I would not poke the bear in general and not buy in HOA but if you are bent on doing it, I would consult a RE attorney that specializes in HOA.  

Often times the only bill that is tied to a house is a utility bill (not power or cable which are associated with a house but tied to a person and not the property) and the new owner takes responsibility for it at closing when they take possession of the house.

Hey Jason,A master lease to a reputable company may very well be a good option.If you are looking to do LTR I would suggest a move-in special. 1/2 Off the first month's rent, etc.Are they all the same layouts and finishes?

It's hard to convince a Seller that their prize possession isnt worth as much as they think it is.Out of curiosity, what valuation strategies did you use for the hotel?