To that effect, I'm thinking of offering to cover half of the excess usage ($500 for Jan/Feb - $100 Normal Usage = $400 split in 2).

Just depends on what your comfort level and willing to dive in the deep end.If your open to higher price range I would tell you to try and stay in the multifamily since it helps offer more rents per month under one mortgage, tax bill and insurance policy.

My goal is that in 6 months I have legit offers on the table for rentals or other real estate ventures that allow me to move away from education.  

My 22 year old relative is putting in an offer on a condo. 

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.

All the things they offer are services you can do yourself; email the cleaners, message the guests (which requires you give them your Airbnb login info), contact service providers if there's an issue, but not from a network of providers, just Google apparently.

Not sure if anyone is aware of Baltimore, MD offering vacant properties for a $1, however needing $90,000 minimum for rehabbing. 

Plus like I said it's a win for the local community to have housing available for traveling medical professionals.

I’ve made 2 offers below asking and she’s willing to take asking, with some wiggle room for the occupancy.