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.

This cycle has played out numerous times:Mobile Home Park Residents Lose HomesMidfield Mobile Home Park Residents Lose Court BattleLoss of Another Tempe Trailer Park Highlights Lack of Affordable HousingMobile Home Park Residents Face HomelessnessIn an effort to preserve our country’s affordable housing, it is our duty as community operators to keep Lot Rents in line with the market rate.

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

It rents for $1950 and is more of an appreciation play because I like the area. 

I don't know if this is in play for you or not... but it could also help explain the significant jump in taxes if it applies.I would start off with a call the appraiser and discuss the situation.  

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

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. 

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.

It takes a lot of time.Do you think a NFL quarterback learns everything over a weekend when they are just getting started, and that is after they had been playing for 8 years at different levels.