In my tests, at least, a service contract like a listing would automatically end, but a purchase contract should be honored by the estate unless the court decides it shouldn’t.

There is likely a phone number and persons name that will come up, that you can reference, since he is having bills that arrive to the mailbox and packages to the door with his name on them.You could make it a pre-condition to the seller that he allow a background check on the tenant before closing and your offer is contingent on your approval.Neighbors typically know what's going on in the neighborhood and will know who the guy is and if he is a trouble maker.He probably has a car and a private detective can run the plates.And so on.The information is readily available is the knowledge is worth knowing.

There are some insurance things that don't impact you, like windshields for cars.

This includes subleasing his bedroom while at ucsb and sleeping in his car.  

Is this an automatic no go?

This is to protect yourself so that if a second offense occurs you can automatically move to evict should you choose to.

We have an existing 5 car garage which I plan on converting into two ADU’s, and an existing 400 - 500 sq.ft conditioned space that is currently not being used for anything.

During heavy rains, which are common in Florida, tenants almost need to wear waders to get from their cars to their apartments.The roofer does offer financing, but the rates are comparable to what we can obtain elsewhere.

Saved a ton on my monthly expenses which I blew on cars and car parts.

A lot of the online calculators will automatically input 5% for both capex and maintenance and then you can usually edit it if you use a different number.