However, shingles are only replaced when damaged (such that the roof leaks - or is in danger of leaking soon) or when missing.

It is a subtle but important distinction.

If you can't stand the idea of walking away from this house because you are emotionally attached--this is a danger sign.

Called an L3C, it is an entity distinct from an LLC.

Look up Venice Ca it use to be called ghost town because nobody would go out after dark because it was to dangerous.

There is NO de minis in federal law and the feds were specific about that in their Final Rule on the SAFE Act.Moving past the SAFE Act, there are a host of federal compliance issues that people have ignored in the past that just can't be ignored anymore without significant risk, and some relatively new ones that can be very dangerous to ignore.

In dealing in title and lien issues, it's dangerous to "assume" anything.

The reason I wanted to have the property in the LLC name was mainly so that the rent check would be to the LLC as opposed to my personal name for privacy and business distinction purposes.

IMHO, its dangerous to try to do a super detailed analysis.

My SO said he has heard of similar things in the past and even though it is not the town’s responsibility, because it is creating a potentially dangerous situation the town will sometimes do the repair and put a lien on the homeowner who won’t pay.