We picked Jake and Gino and it was the best decision we have ever made. 

I would treat him like any other tenant applicant: run credit and background check, complete application, check references, verify income with employer etc. and make a decision based on this info whether or not to add him to the lease.

Metrics like these could possible help in the decision of whether to keep it local or long-distance.

Best decision I ever made.

That's not really helpful when it comes to making a decision.

This isn't to say make bad investment decisions or reinvent the wheel.

I think this might have been hinted at in this thread but if you are going for a purely financial decision, and want to do STR, I would stick only with existing tourist vacation destination locations that have been that way for some time.  

@Eric Oneill You're already making the right decisions and asking the right questions so keep it up. 

Best of luck with your decision!

So its about making the decision to do what it takes to actually be free.