The smaller PM was sold to the biggest PM in the area and they honored the contract terms from the original.  

The biggest expense to the association are water and sewer dues.

One of the biggest being how to find local wholesalers that I can network with.

One of the biggest being how to find local wholesalers that I can network with.

This seems to be the biggest hurdle.

@Jay G.There are a ton of different variables in this situation but I guess the biggest one is why are you with the original realtor? 

In those areas of Florida you're probably buying houses on slab with public water and sewer, which erases some of the biggest issues you'd want to get inspected. 

biggest tip is not to fall in love exclusively as a realtor.

I don't think it's in one's best interest to wrap up a property that limits your buying pool even more than it already limited by the type of property (condo and its 55+ and no FHA) in my opinion this can create a headache one selling as you mentioned.I think your biggest focal point should be how strong are the HOA's financials then how well is the property being maintained.

Obviously location and strategy will be the biggest determining factor... but everyday we are on the forums we learn more about how you pros analyze opportunities.