But Baltimore is one of the cities I'm considering for my 1st investment because a) NYC where I live is too expensive a market for me b) my girlfriend will be attending Johns Hopkins next semester so I'll be spending a lot of time there.

@Jason Hatfield I get more excited about business principles each semester.

Basically, as mentioned above by others, there are a lot of yellow flags for the following reasons:-The tenant may want you off their back so they can participate in illegal activity -The tenant may want to STR the property (not necessarily a bad thing--you can actually make more money this way by partnering with a tenant to do this--it's only bad if they are trying to do it without disclosing to you and obtaining your permission to do so)There a couple a reasons why someone may want to pay rent upfront with good intentions:-Perhaps they are a student who took out a loan for student housing (or their parents are footing the bill and wish to pay for the entire semester/year upfront)-With today's housing shortage, perhaps they have had so many issues competing for houses they want to remain competitive with other applicants in this market by using this negotiation tactic The way to protect yourself is to do exactly what you and others said: solid screening/background check and if it were me, I'd also ensure my tenants knew I'd be doing lots of (legal) checks on my property through the year.

Midway through the lease, and at an upcoming new semester, they didn't get the course load they had received in the past.

Miss that, and you can be toast for the semester or year.

In other words, the child comes up with the cost of the first semester and pays for their books, etc. then when the semester is over, the parent reimburses the child what the child paid for the class on a sliding scale determined by the parent.

At about 40% below median rent for the area.Also, when they expire are at a key time of the year when college students return for fall semester.

I am 22 right now and have 1 semester of college left.  

Two semesters in I dropped out, I didn't see what I thought i would in school.

You could do an entire semester on the uses and abuses of CAP rates ...