I'm also in MA, and before I decided to invest out of state I looked at lots of triplexes that were 1/3 the "book value". After looking at them I could see why! From having all the copper ripped out of the walls to a bio-hazard in dog feces to major structural problems (previous fire, then water damage, and foundation damage) there were tons of them that I wouldn't take no matter how cheap they were.
There was one triplex in Worcester that the owner was asking $300k for (valued at $400k on zillow at the time), and I remember I wasn't interested at the time. Then my agent said the sellers were desperate, and would consider ALL offers. So I said $100k, contingent upon my reviewing the building again since I didn't remember it. They accepted, so I went to look at it again. Boy was I glad I did, even at $1k it wasn't worth it! I passed on that deal.
There was another deal in Pittsburgh that I passed on that I got the seller (wholesaler) down to $2k for, but I couldn't get a contractor to give me a bid because they were scared of the neighborhood (I tried 5 different contractors)!