The first year was tight because of higher interets rates, but his tenants effectively covered about 70% of his living costs.

If you hired an agent or a broker to work with you, you'd be covered - but regulations & laws vary from place to place.Screening is best done by establishing a set of guidelines to qualify applicant tenants, then sticking to those rules to avoid legal issues (and for your own sanity).

And you avoid things like damaged properties (guest insurance from airbnb or prop manager themselves cover that), evictions, collections, etc.   

Interesting that this isn't covered with the "masters".

Orange County, FL is a covered disaster area listed in the above notice. 

It seems like your ROI is basically the same in each option, but you are taking on a much bigger project to convert a single family to a four-family.So basic calculations, since we don't have a full financial picture, i.e. what does financing of each look like?  

The deal seems to pencil, but the bigger picture stuff makes me nervous. 

If I understand correctly, you're suggesting that we should focus on the big picture rather than getting caught up in minor details?.

Only mortgages as debts which are covered by rents.

If the work is not 100% complete by the end of the Escrow period, may implement a .50% (on total loan balance) extension fee that will cover an additional construction term of 60 days.