Ultimately, every applicant is a risk in one was or another, no one is 100% guaranteed or qualified, you could have the best applicant on paper screw you over, or even pass away, you just need to do research and use common sense in my experience.

It would just need to be a situation where they have great contact with the person doing that managing of the project (I.e. have known the person for years, great reputation, person has experience in flipping etc.).

Also just look online and steal some ideas...I used to Google Luxury Kitchens and then figure out how to do the same for less $$.You'll be fine with your experience.

In my experience Vrbo has buried Airbnb. 

Property managers can make or break your out of state experience.

That's looking at it through a narrow lens though, when you zoom out to 5-10-15 years down the road and calculate the difference, in my experience the appreciation has been far more beneficial than the $200 difference per month in cash flow from a different market.

Ask how many units they manage and how much experience they have.

So not much advice, but feel free to experiment and ask your guests to give you feedback. 

(In my experience.

Has anyone had experience with coaching?