If you're in Boston and the surrounding areas building high end homes you should be planning on 300/sqft. 

If they do not know condition of property, your going to have to go and find out, so ask how you can access house, go out there with a contractor and find out (this is going to be hard for you because of distance (4 hr drive) and being your first deal im sure you do not have a contractor.Theoretically take ARV-Payoff-Fix up Cost=Potential profit.

I have driven to that branch from Joppa, Md myself on several occasions on an infrequent basis not a bad drive.

Keep in mind sometimes people say that to try and drive the price up and get the most for their property but I look at it like this, if she truly had such a high offer why would she still entertain you if you low-balled her?

There are several that have discussed investing in apartments (if you haven't already listened to them driving to the lake and back :-)

We've noted a significant reduction in the number of HUD foreclosures available for investors to bid on in Cook & the surrounding counties.  

Driving for dollars.

With that being said try to drive your score up higher than what the lender requires is my best advice.Good luck!  

Drive the streets and learn about the tenants.  

I could probably get some good information from the surrounding buildings.