Ryan, I'm having the same problem with multi's in the Haverhill area and generally around MA and NH. The #s make you want to ignore planning for expensive and short cut the numbers to make the seem favorable. I've had an agent pushing me in that direction (Haverhill multis) for a while, but I haven't found a deal that makes sense, despite his claims of how great it is. The #s might seem good until you have to replace a water heater, a roof or repair leaks from ice dams (ahhh winter is coming). Once you take a few thousand dollar hit to your monthly cash flow you'll wipe it out.
I'm trying to think more creatively, like units I can get for cheaper because they're two beds, turn them into three maybe... units that are unlivable and need an upfront influx of cash to upgrade and get higher paying tenants in (though that cash counts against profits too). Frankly I'm still inclined to take the leap on the right place and try to minimize expenses, but I'm doing a lot of analysis still before deciding that as well as looking at other ways to spend my money. Don't really want to do out of state, so would my money go to better use in a flip, into commercial, etc.? Tough in our area with the market at such a high right now and risk of overpaying for stuff.
the final thing i keep hearing on the podcasts is make low ball offers - can't hurt especially if somethings been sitting on the market for a few months. if its gone beyond 1 or 2 months they'll probably at least talk to you. a few of the big time podcast folks say if you're not embarrassed of your offer its probably too high, and we all know the old saying - you miss 100% of the shots you don't take ;)