But you won't know until you take that first step.To use a basketball analogy, you're dreaming about playing for the NBA when you haven't even tried to play a pickup game at the Y.

One thing you might want to consider is partnering with microsoft and adding a third party app to their office 365 suite of products as they have an accounting arm and many other applications already in play that you could add on just for property management and it would work on their system to integrate everything.

I am not an attorney and I don't play one on television.

Keep in mind, if there is enough depreciation (IRA can't take the bonus depreciation, need to use standard depreciation schedule), that depreciation might negate any positive income.

However, bonus depreciation doesn't apply abroad; instead, the Alternative Depreciation System (ADS) with longer periods is used.The Short- Term Rental Loophole Explained (biggerpockets.com)

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. 

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

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.

Not sure how big the lot/driveway is, but that actually sounds like a bonus to you.