I played professional baseball for 4 years and don't have any experience in the real estate world.

If you trust your contractor and can stay on top of the project, you might not need a property manager my understanding is the property manager is playing the contractor's role for some smaller projects, not another layer on top of the contractor. 

You'll often see variations in minimum night stays, use of 3rd party management companies, and general attitude toward STRs.

Are others playing the long game and hoping for appreciation or is there something I’m missing with the economics of North Jersey?

His criminal record shouldn't play a role if he was released from prison five years ago and has held a steady job, has good landlord references, etc.Disorderly conduct looks pretty minor, and I don't see how it poses a risk to you.

Do you think the high property taxes play a significant role in shaping your investment strategy moving forward?

What lists are you targeting plays a large roll also.  

We have bought only a handful of 2nds but to me, the 2nds game is a volume play.

So I wouldn't see how 6 months would come into play on this. 

You're developing plays at the collegiate level, but you haven't even played a pickup game with your buddies to see if you like the game or are any good at it.