You could do MTR during the school year and STR in the summer, but I would want to take advantage of football Saturdays during the fall so maybe you pivot after the holidays? 

That sounds like a great plan to get started out of school.

Aside from your typical items like budget and area, I am looking for something in a good school district, and a moderate size in terms of bed/bath room count, as well as area.

Prices and the interest rates were part of the reason why we decided to wait. elementary school ratings and career changes were the other things.As you suggested, buying a fixer upper is also an option. concern with that will be the added delays in actually renting out the house after the fixes/updates.

I just got accepted to MCPHS medical school in Boston, Massechusetts.

Nashville is home to two major medical schools, Meharry Medical College and Vanderbilt University Medical Center.

Generally I look for median homes price & income levels close to good transportation & decent schools. 

Population growth, strong job growth, multisector industry/economy (Never invest in an area propped up by a single industry, or worse, a single company), landlord and business friendly, strong development, strong sports teams (even minor and farm teams), lower crime rates than national average, and good schools/colleges nearby.

Consider it paying tuition at the school of landlording and move on.

I live very minimally at home currently, still with my parents, so I would only be spending about $350 a month total, including the loan (assuming I can get it for the time period I calculated, which is 3 years), so I would still be able to put aside about $11,000 for school, a car, and the downpayment for my first deal.