Tom
Im originally from next door in Medford...I own and manage 20 rental units on the North Shore and i watch the multi family market north of Boston very closely...
our market is a lot different than most of the rest of the country with the exception of the NY/NJ and Cali as well as a few other markets...so you can forget about singe family rentals around here in Ma unless your willing to travel at least an hour West or even down to RI...
Now on to Multi Families...If you want to find cash flowing properties around our area you will need to focus on areas other than Arlington or Medford...Its even hard in areas like Malden or Everet which are great rental areas its just the good multi's are still selling for high $300K's and well into the $400K's...
id be looking at areas like Chelsea, Revere, East Boston or Dorchester which if you look can find a 3 family for $300K with 3 bedroom units...now, if you rent to section 8 tenants you can take in $1500 per unit...i believe the #'s work well in that type of scenerio and will provide good cash flow, cash flow like we havent seen in awhile here...now if you not ready to deal with section 8 type tenants than i have no other advice for you in our area...good luck