The idea is they want to add more long term rentals to the market to help with affordability.The mid-term market is interesting but then you are covering utilities, internet, etc.

My strategy is to use HELOC to cover down payment and convention loan to cover the rest of the mortgage.

I'm about to do a rent-by-the-room/co-living property there, since current LTR rents don't cover the mortgage with these interest rates. 

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".

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?  

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

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