I've talked to a few architects and dug through the code a bit myself but can't find anybody that really deals with this type of issue as it seems very niche and specific to three-families.

Additionally, the roof replacement is definitely the time to add insulation, and adding enough to meet local building codes is just as easy as having less, assuming a tear-off. 

I would suggest zip codes 33607, 33614, 33616, 33609 and 33611.

Strictly numbers it looks good.

There are plenty of Hard Money Lenders still lending however just as others have said they are taking more risk now therefore the terms will be more strict then they have been to mitigate that risk.

Probably too late at this point regardless, but there will likely be building code issues brought up (fire exits, clearance heights, non-permitted improvements).  

Have them put an electronic lockbox on the unit with temporary access codes.

For those needing information in the future, read the US Code and Dept of Justice website.

I have had over $12,000 in losses from cancellations where airbnb broke short-term rental contract terms and conditions (strict policy 1 week before check-in, 50% before).

I just opened escrow on a duplex in Los Angeles (zip code 90037), for $610,000, I am freaking out!