New investor looking for buy-and-hold in MA

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Hi all, 

I've been considering getting my feet wet in real estate investing for years now, and only recently begun to consider myself financially (and mentally) ready to jump in with both feet.  

For my first purchase I'm targeting multi-family properties (2-4 units) for buy-and-hold (cash flow).  I'd also like to find something that doesn't need a whole lot of work up-front and would attract a more steady and reliable tenant base.  While anyone from Massachusetts will agree that inside 128 is great for long term appreciation, it seems like not only is it astronomical in price, but also not so good for cash flow.  

That being said, my research is showing that Worcester, Leominster, and Fitchburg all seem to have some quality multi-families that can potentially produce some good cash flow.  Even Springfield seems to have some promising opportunities.  My difficulty though, is that being born and raised in the Boston suburbs, I'm not familiar at all with those areas.  

I'm looking for anyone's advice on whether my thought process is sound, as well as welcoming any feedback from folks who may have gone down this road already (or are doing so currently). Is what I'm looking for even out there? I see lots of opportunities on MLS, but I'd hate to be leaving something off-market on the table. I'd love to connect with anyone looking to brainstorm or trade thoughts and ideas as well - and I'm always down for a cup of coffee, weeknight drink, or weekend lunch.

Thanks very much in advance!  Looking forward to your thoughts and advice

-Phil