Welcome Tatyana,This site is really excellent and good luck with everything. 

Excellent advice Account Closed !  

I suspect his volunteering is partially motivated because I told him when he moved in at the beginning of this year that I'm inclined to reward excellent tenants with a rent rebate around the holidays (e.g. half off december's rent).

House is in excellent shape and needs, at most, interior paint.

If you would like to give some context as to the factors that you look at in priority order (more important factors vs. less important factors) that would be a value added conversation as well.Additionally if you would like to provide some flavor as to what kind of ranges you are seeing regarding re-performing 2nds and the factors that influence your buying decision, that would be excellent as well. 

Make a digital package and some paper copies to bring with you.

This is an excellent question for your CPA.

I know this an excellent deal, but my concern is locking up much more money than I originally anticipated which will severely push back the timeline to purchase my own home and it doesn’t give me the ability to scale/capitalize on future opportunities when they come up. 

It’s an excellent place to start, and can answer many of your questions.

The benefit to GR is you also have some excellent secondary markets to purchase cashflow (Lansing, Muskegon, Kalamazoo).