And if they don't deliver, you need a truck and an extra person.  

Just ask the person straight up how they rate themselves in terms of looking after a home and what they say and the nonverbal cues will likely tell you what you need to know :) 

And technology aside, this business hasn't changed much in the last 20 years.

If you’re looking for more insight on RRG or your particular STR deal, I’d say most people on BP would agree that I’m the go-to person here for that.

The answer to this question is really a personal one. 

In addition to real estate, I’m passionate about entrepreneurship and business development.

The downside will have more to do with your business personality.

Personally, I love working with distressed properties, especially foreclosures.

Quote from @Michael K Gallagher: Quote from @A Rao: I invest in land and have done entitlement/zoning and other DD work successfully for years.A broker called me this morning on a property I have on a busy interesection and has a QSR client who likes the location, but does not want to do a ground lease, only a build to suit. 

You look like the kind of person who is going somewhere.