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.

If you want to attempt to rep yourself, you have to play the game too.

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

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

Thats what I would do next and you can really just see what the numbers tell you (and look at different rate/refinance scenarios how it would play out in the next few years)