If your numbers are not working...go up;  Meaning, better properties w/higher ARVS in good neighborhoods/schools. 

My kids are pretty settled in their schools and it would be hard to uproot them.

The holidays are a magical time, full of family gatherings, laughter, and... real estate deals?

Look at crime rates, school quality, vacancy rates, and rental demand in those areas.Talk to Local Real Estate Professionals: Connect with real estate agents, property managers, and other investors who are active in the specific areas you're considering.

Evan took an online class and learned how to replaster walls and yes I do mean old school plaster.

Good neighborhoods, excellent schools, and literally--where does the house I want sit in the actual neighborhood...I say does it look like a $650K house area when I'm done?

For the former, being able to add 25% more units to the right apartment building is just magical.

I agree.. just look at any large mid west or rust belt metro.. there is a ton of houses avaliable the question though will folks buy in certain neighborhoods where inventory is readily avaliable you can buy existing in many of these markets for far less than new builds.. so to me its really a neighborhood issue  a school issue a crime issue etc etc..

Since he doesn't seem to have been able to acquire that sense through the school of hard knocks, he's not going to acquire it through sweet reason spoken to him out of his landlord's mouth."

It's not a traditional school building.