How much weight should I give to timing the purchase around the students? 

A good one is worth her weight in gold!

How much weight do you give that map on making an initial decision?

It would be a win win cause we would be staying rent free and he would be saving on utilities and upkeep.

But I have some potential hang ups - Building is OLD, 1900s-1920s ish, agent/landlord has ownded for past 10 yrs and has done minimal upkeep.

It sounds like you'll end up keeping all hf their deposit and might even need more to make yourself whole. 

I have found that a lot of the homes I end up keeping for my personal portfolio are ones that do not fit into our criteria for our turnkey business.

This is a pet peeve of mine . ..I’ve heard many times on here of heating and cooling units failing because the filters weren’t changed or units not inspected etc .. folks you can’t rely on tenants to do this stuff and you can’t force them to pay for upkeep of the systems .

And for some of the work, we would of needed a contractor since we don’t have the experience or expertise to remove weight bearing walls.

You will also want to understand common area maintenance, especially if you are targeting 3 units or more (lawn care, snow removal, cleaning and upkeep of common areas, etc) and understand the parking situation.