Here are some other things that could go wrong which may cause failures:Unknown necessary repairs (i.e. sewer lines, roof, etc)Not having cash reserves to cover vacancies / major repairsUptick of crime / vandalism in neighborhoodVandalism of propertyInfestations (pests, other)Bad tenants / No tenants / tenant family issue impacting stay (i.e. death, divorce)Rezoning of school districts / Loss of accreditation of school district Insufficient Property Management (not addressing tenants concerns, no notification of repairs timely - causing further damage, etc)Not following market pricing on rental / raising rent to frequently or too much at onceLegal issues (i.e. tenants sue for injuries on property, taxation, etc) I think you get the idea.

Property is in a c- minus area.  6 units all 2 bedrooms, Farily new roof/boiler,, etc and not much rehab needed. this is mostly a turn key property.

Built in 1980 Roof is 10 years old. 50% of the A/C units are new.

How is the roof and foundation? 

I do have money saved up but all that is going to rent to keep a roof above my head.

Looking at listing may not need full rehab, new roof and water heater done, 3br in neighbor run 900 to 1000, rehab for low maintenance, try to buy as low as you can , look at comps, probably could go in as low as 38-42 with good agent and stress as is, maybe a few agents here to help, get one to give you good numbers not listing agent numbers , street is a nice one for area, not much back yard or parking but nice front, before you close make sure vacant  contingent, if numbers work I would do it, the are predicting an abundance of rentals avail next year with building craze but keeping expense low you should be safe, remember don't rehab as if you are living there, think durable and repaintable, number should go into systems and structure first, elect,heat,walls, windows,floors,plumbing, if you use a contractor go with one you know or work with someone in area to keep an eye on progress, good luck at least you know some of the history of the property

Feels like a good deal (nice lower income neighborhood, bike paths, parks, 10 minutes from personal residence ) but the AC and roof may not have too much life left.Based on my analysis, I think the FMV for a 2/1 like this is closer to 35k.Inspection in a couple days - planning on asking for $3-5k back at closing to a) mitigate risk of roof/hvac replacement and b) bring purchase price closer to FMV.Is a deal like this worth walking away from if I don't get a concession post-inspection?

The roof, sagging floor, and electrical improvements i cannot do.Thanks guys

City water and city sewer, metal roof. 2 units currently have tenants in them and one of them includes a garage bay in the lease.

I've heard a bit about East Boston, but you're right- prices are going through the roof in that neighborhood.