There is a lot of crossover between PA and DE in terms of lenders, agents, contractors, etc so contacts you meet at DIG could still theoretically be useful to you in DE, and vice versa. 

You aren't gonna be doing anything measurably better or worse by picking Cleveland over Indy & vice versa.

Assuming this service would be able to provide a captain so you don't get random drunks steering your yacht... 

In my opinion the cap rate speaks for itself - lower cap rate stable income less headaches, and vice a versa.

Try trading up with someone in your market(Like literally sharing your buyers with someone else and vice versa). 

There are plenty of deals out there and you will do better in the long run with an attitude of abundance and helping people, vice scarcity and hurting people.

Once I import the VRBO calendar to Airbnb and vice-versa, I should be good to from there on out, right?

And vice versa.

Fail to be the captain of the boat, and anarchy ensues. 

I wound up on the water instead as a boat captain.