While to be Boston proper you are looking at some areas that are $1000/square feet you can find a lot of value in some metro areas such as Roslindale - 2 family with 5/6 beds can go for 5-600k in fair to good condition and that’s a nice middle ground location.

@Brandon Swartwood I would recommend starting with the ULI Guide To Professional Real estate Development.

If it isn't properly insulated it could compound the issue with costly electric heat. 

My friend is a real estate developer who has successfully bought, renovated and sold/rented out a few small apartment buildings in the area (I live in the Bay Area so there are plenty of 4-8 unit buildings).  

They do property development also so they are used to working with investors/developers.

Maybe not responsible for removal costs but you should get your money back, since you paid for a service that they did not perform properly.

Thus, the Department believes that in appropriate circumstances, owners and managers may develop and implement reasonable occupancy requirements based on factors such as the number and size of sleeping areas or bedrooms and the overall size of the dwelling unit.

What’s the proper way to continue this conversation?

Then take next best highest and use tenant and figure out rent per sq ft they could pay.You could possibly sell the land to an end user tenant, sell the land to a developer and make a spread, ground lease the land, or do a NN or NNN lease and construct the building.You need to analyze the tax implications of selling outright and paying higher short term gains capital tax versus developing and then converting to a new value created loan of 65 to 75% LTV.

Also, I wanted to see what are implications including for the holding cost if this is part of a Planned Unit Development community.