@Matt Everling I wanted some diversification outside of my Florida market and I looked at the up and coming areas in the midwest with good potential for stable cashflow and lower entry points.

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

@Joel Scarboro You have the potential to benefit from a cost segregation study, but determining whether to do a cost segregation study or not has a lot variables. 

Use BP Calculator(s) to show the potential investment returns.

The area around it is the fastest growing in potential revenue per sq ft.

I wouldn't touch Cleveland personally it can't and shouldn't' be compared from an ARV potential it's a cash flow market strictly. you can't do the strategy you are talking about when the average home is more than 60 years old in Cleveland and sells for $120k or less. hard to change those economics.

One potential way to structure a scenario where a long-term tenant of a single-family home can receive homestead exemption is for the homeowner to designate the tenant as a co-owner or co-borrower on the property.

This is anecdotal, as I haven't done this myself (yet), but that's what I've seen.What sources are you using to find your potential tenants?  

I was wondering if anyone in my area had any deals in progress, and would be looking to potentially collaborate in some way? 

That leaves me to private lenders and the mortgage broker that approach the few that he knew in the Island were interested in doing a loan not a Line of Credit and Biggerpockets is not big in Puerto Rico although that's a potential market.