If you do your research, an out-of-state investment can work, but you need to know exactly how to hire a PMC (most get this part wrong) and you need to ask a vetted PMC what they would buy in the area and what it will rent for. 

I have seen all sides of this equation, self managing my own properties locally, but moved with the Navy 1000 miles away and managed the same rentals from afar, and had friends here in Memphis that had 18 properties and had them all with PMs with varying levels of success, some bad and some great.Self-managing brings about an additional level of responsibility that most of the time is fine, but that is not what you hire a PM for.

You hired someone to do a service for your benefit , YOU pay . not the seller 

I would have hired a junk haul person to do the clean out instead of my contractor.

At what point should I hire another me?

Thanks to COVID, for a couple of years, you can actually make enough money to be cash flow positive even if you hire a property manager AND have mortgage payments. 

Hiring a manager or Pad Split still means you’re in the BUSINESS of running a rooming house. 

My place is in Castle Rock, just south of Denver.

This is part of being a landlord - if you can't handle it:1) Sell2) Hire a PMC

But when people are out of town / out of state the title company can hire a mobile notary near you and they will fedex the documents to your local area to sign.