I think your timeline is critical in this evaluation. 

I'm thinking about a 203K.

I think now is a great time to buy real estate in Florida.

@Agustin Conti In the case of these repairs to the driveway and patio/deck I would think they are solely cosmetic and at your discretion as to if you will pay for them unless your insurance company has flagged it and told you to repaint it or repair it which you did not mention so I will assume is a no.

I think its very interesting to see developers like National Real Estate who are wrapping up the 15 story development on 2nd and Spring Garden saying their next project on Spring Garden is simple a matter of time.

And what do you think the timeline would be before building to rent would make sense again? 

Most professionals will recommend a separate LLC for every $1 million in assets but I don't think that's necessary.

They’re going to want to see leases or underwrite it well below what they think it can rent for.

I'd think even where sub to or seller financing is most common, maybe the markets where it happens the most, maybe it achieves 2 or 3% max.The few times I see it in our area personally, is almost always on a 5-10 unit non-performing asset that someone can't get a loan on because of the debt coverage requirements.  

@Alecia Loveless is not (I don't think) doing a legit Home Inspection with legal ramifications and all that (Inspector gets sued becuase he missed a pinhole leak somewhere for instance).