Once you know what it is that you’re looking for specifically, it can help weed out potential deal breakers.

Replaced 24 old, rotted wood windows with new low E vinyl windows, replaced 9 old broken wood exterior doors with new steel security doors w/ master key deadbolt system, added one bedroom w/ lighted closet, and lighted closet to existing bedroom, 2300 SF of new carpet installed, 700 SF of engineered hardwood installed, 3 new water heaters, 2 new exterior electric services, 2 new interior breaker panels, new paint on all walls and trim, 4 new shower surrounds, 4 new countertops, 4 kitchen sinks.

Replaced 24 old, rotted wood windows with new low E vinyl windows, replaced 9 old broken wood exterior doors with new steel security doors w/ master key deadbolt system, added one bedroom w/ lighted closet, and lighted closet to existing bedroom, 2300 SF of new carpet installed, 700 SF of engineered hardwood installed, 3 new water heaters, 2 new exterior electric services, 2 new interior breaker panels, new paint on all walls and trim, 4 new shower surrounds, 4 new countertops, 4 kitchen sinks.

I don't think this would have been a deal breaker, but from the planning board "to have a building that already exists, that was built for human occupancy, but not currently used that way, seems contradictory to everything we're trying to do here in the city.

They called me the other day (Sunday) saying there stove didn’t turn on and they thought it was the breaker.

He can afford the property without the additional income it's not a deal breaker. 

The Lead laws can be deal breakers and the laws in MA are generally more favorable to the tenant vs the landlord. 

This would be a key factor and a deal breaker.

you need to talk to an attorney and also do some calculation to see if it is a deal breaker with the water/sewage bill.

But, it did require several thousand dollars of work including a new sub-panel, new circuits for lighting, the ceiling fan in the Living Room, 220V service to the relocated laundry center on the main floor, some additional lights in the basement and all of the lighting for the front porch.