in the opinion of others with more experience than me in this type of situation, is this wise? 

Just closed a loan with this exact situation.

Up keep is minimal in my view but depends on ones situation and time.

I am looking for advice and/or ideas on my current situation.  

The fact that you're investing from a distance doesn't improve the situation. 

The Federal Government also added a "stress test" on new mortgages.  

Unless he's a skilled painter and just sees it as a mutually beneficial situation, this sounds like a huge red flag ...... proceed with caution.

Like Landon said, good on him for admitting hit; honesty in a tenant is a very good thing.The only issue, and I don't know enough to speak to it, is if you accept him as a tenant knowing that he has a misdemeanor, is there a way to get into a discriminatory housing situation because you selectively enforced your own rental criteria.  

First off I will describe my situation as best as possible My fiancé and I are looking to get in to real estate. 

I would start off with fewer units (around 18) then large complexes later unless there are plenty of homes that have tri-plexus and four-plexus that are occupied will cover your debt payments and possibly allows you to live there if your situation would allow you to possibly live there.