I know I am letting emotions play a role in this but this is our personal residence and the security on that and for my family is very important.

I have been playing around with tenant cloud and seems to be a simple option for a small business.

I have a masters degree in city planning - I know how cities work, how citizens live / work / play within them, and how to use government to your advantage.

Don't skip the process in vetting this person, and be sure you can deliver; if not, he will play the "blame game."

It is a waste of your realtor's time not to mention playing with the sellers as you aren't going to buy all of the properties.

There are investors that gamble on transition areas.

Playing the social justice crap of roommate meetings to talk about stuff that doesn't matter makes me think this person is likely to try to play games.You might try to be helpful and do some searching for/with them, print out listings that are in the price range as what she is paying you, etc. 

Playing the long game in a stable market is smart.

Once you have that number (maybe it ends up being $160k, maybe it doesn't), take 70% of it (or maybe even 65% if you're new to the process), then subtract your renovation, holding and closing costs, which will vary based on a number of factors.In your case, let's play it safe and say the the home ultimately sells for $150k. 

I haven't been there but my nephew plays baseball in Chicago.