In addition, you could advertise as a house hacking opportunity and possibly command a significant premium considering supply is so low in many markets around the country. 

These properties command a premium in price when purchasing (think double) and offer much more liability.Orlando is a great area for vacation rentals, but I can't really comment on standard SFR rentals in either area as my primary focus was on a primary residence, not rental.  

I'm a 28 year old single father who like most of us, followed the route we were told, earned my degree (Mass Comm) and left with a piece of paper and $35k in student loans.

IMHO, the real value is in the rehab and forcing the appreciation in the property which also commands higher rents assuming you're in the right market.

Rockville itself is a bit run down and doesn't command great rents.

You can get renters in other seasons however you also can command a better price during a season when there is more competition for rentals.

Property is well kept and commands top rent.

Just be sure and inspect them, if you let them put in their own.But, any apartment with either a W/D in place, or hookups, will be more desirable to tenants, and command a higher rent.

Hmm; Just because the school year is short and you get a full 12-month lease, doesn't mean IMO, you will get/command a full payout on those terms. 

Every penny counts right now, and I would rather have a vacancy in this property one year from now when I have the ability/bandwidth to deal with rehabbing units and showing the property and getting a new tenant settled - plus the location is changing quickly and will command much higher rents in 1-2 years than now.