Unfortunately, my monthly income matches my expenses (97.%!)

Yes, the sq. footage doesn't match the comps so $1700-1800 is probably more accurate.

I also asked the HOA to confirm if my understanding of what the contractor told me, matches their understanding of what the contractor told them.

Obviously Columbus matches up very closely to what the U.S.

What's your estimate for sprucing this property up to match the 300k property? 

The trim I originally wanted was too expensive and would take weeks so I settle on some cheap stuff that doesn't really match the style of home but whatever, I need to get this done.

They might contribute money to match yours and might bring valuable lending relationships. 

Anybody know of any software that can scrape things like Realtor or Zillow, as well as match fields like Property Tax, and Rental income (comparing to say Rentometer or something)?

Alternatively, if the same firm that is helping you buy is also responsible for managing the home, it avoids finger pointing should the reality not match with the pro forma.

Also, if you are not geographically limited, you can try to match up your talent/interests with an area that offers a more reasonable cost of living. $400k housing and $9k in taxes annual, plus the utility costs there, don't really make Vermont that attractive from a financial point of view (which is too bad because it's a beautiful state).