He likely needs to stay where he is, save up money for a downpayment on his own, and buy when HE is ready.He's not ready. 

Because that is when the impacts are most felt of everything one has to do with the now pile of ashes. 90 days to do nothing forces people to engage with staying. 

I really would want to stay away from any office properties in depressed or even semi-depressed neighborhoods, especially large ones (like a 13 unit complex).

STAY away from them at all cost.

Sounds you have definitely worked hard to make those stay in good shape and steady tenants, which is excellent!

Stay motivated by setting goals and celebrating progress!

So that has been my "next action step" to wait for a clog to happen again and have him camera it, but it has now been almost 1.5 years with no incidents.TLDR: There is a chance that the bottom bathroom tub/toilet could fill with sewage during a guest stay, but I am hopeful that the next time it happens will be the last.

Everyone will tell you it’s great to get started early, or you can just move after a year, but in the current environment in our region the rent your property will generate after you move out will likely be less than your mortgage, if you are tied to the area and feel confident you want to stay in whatever property you buy for 3-5 years go for it, if you want flexibility rent and throw that money into and index fund. 

We'll lose money for 75-90 days but the new rent is market so some will stay and not forcing people that can't afford it to move in the middle of a very cold winter I think buys a tiny bit of good will and is the decent thing to do.

Stay in and be part of this 721 or lose my investment most likely.