You’re going to have to find a specialized function that can’t be farmed out to the Philippines in the $5-$10/hr range.

Everything is functional in the property it is a older home.

Short-term rentals are becoming oversaturated in certain markets plus anti-STR legislation is resulting in some of those properties also converting to long-term rentals.You already have the operations experience by self-managing.

Focus on durability over bells and whistles—tenants prioritize functionality and reliability.

She will probably game the system for the next 6-12 months, but that's what you get buying a property with a non-paying tenant in place, in an anti-landlord city. 

If you purchase in a anti-landlord state, you'll likely have a harder time and deal with extended timelines if the need to evict comes up.

I’m actively analyzing the demographics and rental trends in the area to ensure these upgrades aren’t just attractive but also functional and desirable.

We get inquiries all of the time on Airbnb/VRBO/etc for large group functions at our properties, even if we say in the listing it is not allowed. 

This way we reduce our monthly legal expenses and have cash reserves to weather the next few quarters during the virus.

Your GC will know how to apply for the correct permits.Avoiding the issues in the future is a function of respecting the permitting process in the first place.