Since I bought the property in 2019, I've written off about $13k in depreciation. 

First off, congratulations on the recent graduation!

What I'm really doing is creating a "workshop" space that's part of the house that can be used towards a business write off, but can also be easily converted to living space with plumbing/wiring already installed in walls/floors.

Paying off a house completely is a trap.

If the casita doesn't have a legal address then no mail will be dropped off to it.

So I think my best bet to start off with is to find a property management company.That said, I’m wondering if anyone has tips on property management companies they would recommend, and/or any tips on how to find the best property management.

Your commission split will be higher in favor of the broker, BUT it's a good place to experiment and have your training wheels before branching off onto other brokerages that give you a better split. 

I am also out of state and he is local.We likely will be buying off the MLS and trying to identify something below market value and negotiate a deal.He will manage any cosmetic rehabs, furnishing and then ongoing management of the listing. 

Interest rates on the DSCR cash out arent that far off from conventional financing right now, but the HELOAN rates will be a good bit higher.

The health care traveler market has fallen off and more people are getting into it.