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.

When its fixed, mix up the sack-crete and fill the holes.I'll say the same thing about sheetrock.

I wanted to fill the 'educational' void after studying intensely for months to pass these exams.

I ask this because upon looking around Zillow I found a "residential-single family" home that has 12 bedrooms and the description claims that all 12 rooms rent out and that it's already being filled for the upcoming college year.

I guess you havent been to the grocery store in the last couple years , filled up your gas tank , paid your insurance , or bought a car  ? 

How can I better automate my lease agreement being sent out, information filled in, and then easily signed by the guest?

These questions are usually answered with a form that is required to be filled out. 

In those towns is where the STRs entrepreneurs usually invest, they are mostly digital nomads as well and they come for the summer go when it rains, and when it rains locals fill the spot with some tourist to boot. 

I wanted him to fill out the application and do a credit/income/background check but I'm not sure if he will pass since he has no history in this country. 

Not sure who will fill his shoes.