Here you are having upward pressure on pricing by forces from outside the metropolitan area. 

Other than it being hot in the winter (steam heat; radiators on the ceiling) and later realizing how tiny it was (all the apartments in the building was only about 800 square feet) I remember the only problem we ever had was the risk of the toilet overflowing during very, very heavy rain storms (dad built some type of wooden contraption to place in the toilet during heavy summer rains to push pressure on the water). 

No pressure, just nice people. 

My wife’s a realtor and can send you auto listings if you need, no pressure just offering her service.

In any event, the local MLS board (or whatever it's called in your jurisdiction) will definitely be able to apply appropriate pressure to act swiftly.Make sure you request in writing the seller's acceptance or denial of said offer.

I collect cars and if it were not for the occasional release of the proverbial pressure valve, I would utterly burn out.

My first step is just gauging if there's actually a demand for this in my area (Hagerstown, MD).Does anyone have experience with mid-term rentals and estimating demand in their area?

I think there needs to be pressure on teachers and schools to perform. 

The area constantly draws students and young professionals which keeps upward pressure on rents and keeps occupancy high.

This is our first time dabbling in real estate, and I've never seen her experience pressure like this.