Not to say that weeks before the semester starts you can't get tenants but tenants look well in advance and if you don't secure someone  well before the semester starts you  can run into trouble filling the unit for the year with students,  depending on the area supply of course.

You should, get quotes from local Roofers there, that have longevity in the area but that you do NOT hear on the radio, see on TV, etc!

Even back then there were a lot of high rise hotels where you could get a decent condo-style room with hot water, cable tv etc for really cheap ($15-20USD/night).

It could be the water supply line dripping on to the floor.

Some things to be mindful of are the added costs of having to facilitate delivery and acceptance of the windows if you are purchasing them yourself rather than go through a contractor who both supplies and installs the windows.

Or at a local real estate meet-up is another great option.3) IMO (duplex, triplex, quadplex) are best, butttt in some areas supply is limited.

Our plumber re-plumbs entire houses for much less than that, and if it's a simple leak you can find, you could be done for a few bucks.The 80's were the era of pinhole copper, so there's always a chance that your supply lines are shot when buying a house from that time period, but it could be something minor too.

Higher than inflation appreciation will occur where demand outstrips significantly supply. 

I didn't have TV in the 90s so I didn't know about Carleton Sheets and John Beck et al until later.

While I don't supply paper towels, each of the three bathrooms is stocked with three rolls of toilet paper.