If I was in your position at your age, I would want to build even more equity now and consider cash flows deals later. 

Given his age, he already has trouble going up and down the two-story stairs, so waiting longer would mean the guy would just be further entrenched.At the end of March I certified-mailed him the Non-renewal notice with a move-out checklist, and regular snail-mailed him the same thing two documents just to be sure.

you say he is older, make sure there is no tax freeze and that his tax are not lower because of his age and income.

Whenever I take over someone else's building, esp working class (which I would assume this is by the cap rate), I like to estimate first year expenses of 20-25 as well for maint/repair/capex... but I would vary it based on the age of each component and the cosmetic condition of all units w special attention paid to kitchens and bathrooms. 

You're biggest asset is your age.

How Aged and Problematic are the things tenants will most likely call you about.

basements units are easier-   They legalized a bunch of non conforming/ilIegal units to owner occupants right off the bat but are taking a much more stringent look now. 

I know it’s probably overthinking it but this day in age I would rather have too much protection then not enough.

And about 75% of the investor clients I work with are under the age of 35. 

Are you trying to target college tenants or are you in an area with primarily college aged renters?