It's obviously less "risky" to do the small home nearby, but the Florida place comes with potentially high, consistent rental income, nearly year round.

I have my favorite gear classified ad sites and get much better deals at those sites.Note a value add does not need to be constrained to simply rehabbing a property (but that is what my value adds have consisted of). 

They were very consistent and had been there for more than 2 years.

Walk properties and practice what questions to ask, what problems to look for, etc. 

So again, we are using a business practice that works which is limited by how much it can scale, and that once again puts a hard cap on how many units we can run successfully and how passive this business can really be for us.

Will In theory bla bla bla, in practice the only time I've seen someone with the necessary supporting docs, she was a CPA and her boarder was her long-term (12+ months) boyfriend.

The deal consists of five properties on one note. 3 out of 5 properties are currently rented out at 440/mo. 4 properties are 2 bed 1 bath 700= sq ft. the other property is 3 bed 1 bath 900 + sq ft.

Does anyone have advice on the best times to begin advertising, examples of leases in similar situations, and best practices for screening tenant-roomates? 

I know it can be done as most successful people are currently doing it, but any practical tips and experiences would be appreciated.

The UPB is $267k and the payoff is $584k, which consists of at least $260k of deferred principal and the rest being arrears and advances.