I don't know, lately I've been thinking if I would still want to be doing this whole landlord thing in the future and therefore trying to figure out if there was an tax convenient way of liquidating all rental properties and live off a brokerage portfolio.

Take living conditions as an example.

I lived here my whole life and never even thought about wild fire risk.We do get pretty wild and random thunderstorms, hail, and some high wind speeds. 

I wouldn't switch the utilities into my name if there is potentially a person living in the house that is going to run up my bills.

I live fairly close to the Poconos.

You could live in one of the units and use the other $250,000 to buy a multi-unit property, which you would then rent out to pay your living expenses.2.

Hello, I live in Augusta Georgia.

Live and learn.

How long are you going to live in the property before you turn it into an STR?

I will not be living there and there are no other occupants.