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?

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. 

He played on my emotions - it's easier than finding properties and dealing with tenants, PMs, etc.

They make things way too difficult compared to a simpler, DSCR solution.The type of lender also plays a large role here. 

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.

4) Due to all of the above, high chance they start playing games with other tenants, leading to bigger problems.5) What happens if you have to part ways?

I'd look at when the next unit lease expires and you can either...Delay closing until it's expired and vacantGive them another offer that's less enticing to not deliver the unit vacantWhen it has to do with financing the playing field is pretty level, every buyer will be able to get more competitive with a vacant unit