This burnout led to me selling off my rentals, dissolving my business with family, and having my mother take over managing her own units.

This would likely take coordination with a tenant at some point - (ie - plenty of notice to them that they must vacate in order for you to sell the property)Since your current home is free and clear -  you could do a cash out refi or take out a new mortgage on the new house to be able to buy your paren't house and pay off the mortgage.  

We took off the carpet and found plywood underneath.

In the city or more urban neighborhoods though it's definitely more commonplace.I've added off street parking behind a property off an alley like you said at least a handful of times.

Which made my tracking for taxes and such all look super dumb because everything is off by a dollar.

I am leaning toward removal because the floor is run down, the risk of increased pests or feral cats, and there is already a storage closet off the patio.

If you have cash, you could pay off the underlying loan2.

Borrowers overleveraging, deals falling apart, and platforms absorbing starting to selll off these losers. 

Obviously the answer is yes when it comes down to the cash flow, but I am particularly wondering if HCOL/high property tax areas are places you would cross off the list entirely.

There’s not much AirDNA data to go off, so my best guess is it’ll be tied to Savannah seasonality and around ~50-55% occupancy.