I have found a few coops that I could afford in great areas however, I would want to ensure could sublease or do Airbnb (I know that tends to be a lot trickier).

You might have to pay a little more knowing that you have upside ( but take  caution especially as a novice to ensure you are making an overvaluation mistake) .  

His bid was fair and then further reduced because I allowed him to stay at the property during the rehab.

How to get a fair assessment of the property (appraisal?).

@Russell Brazil, your comments make a lot of sense and seems to paint the plight of both sides in a fair manner. 

Most all of the structures are fairly temporary in nature of construction, so down the road, re-purposing the land would be incredibly easy. 

One must develop a comprehensive discipline for analysis and negotiations to help ensure their success in this niche. 

Kensington is starting to explode as well -- never thought I would see the day -- but if you can find a decent block with fair pricing, go for it.

Virginia landlord tenant law is fairly specific about proper steps to take, so follow it. 

We initially signed a contract for asking price on the property and I subsequently asked for $20k break on the price based on the inspection results, which I thought was a fair ask and the seller signed the addendum accordingly.Now the seller is asking me for another $6k to cover costs of heating unit replacements (after further inspections done by the seller as required by the city) since the units are over 50 years old and cannot be brought up to city inspection requirements.