On my trip I have learned that although they are welcoming tourist back because the demand for income is high they are not fully functioning. 

Rent is still due March 1st, in full, and they are free to stay or go.If the junky is a high functioning drug addict and he wants to stay, assuming he can pay the rent on his own, and you trust he will pay, then why not keep him on his own till the end of the lease. 

What clubs, functions, groups, boards, etc are you a member of? 

All functional just like 1980 old.

Both NC and FL are pretty large states. 

If the furnace had some specialized function, such as in a climate controlled self storage facility, then it could be a 5 year asset. 

But if they are high functioning and able to function close to normal then yes I would.

Second story or extension to the original house with a fully functional “wet bar.” 

And the award for most diligent use of the @Mention function goes to ...

As Basit Siddiqi mentioned, its tough to house hack in NYC and live free.I’d suggest you use BP’s search function or set up keyword alerts to see what other folks have to see about house-hacking and other topics you’re interested in.