Mass is a big place. Aviation certainly isn't going digital anytime soon. Unless you mean the Mass State Police trunking system. Yes they're going to a digital system in the near future, system is being built out gradually. An analog only scanner will let you listen to many towns that haven't gone digital, also aviation and for the time being the state police as long as it can trunk. I would advise against spending more than $100 on an analog only scanner as they grow more obsolete with every passing year. Aviation buffs are in heaven though, tons of good analog scanners out there for dirt cheap now.
My opinion- I would say try to pick up a cheap analog only scanner on Ebay for now, see if you like it and what you like to listen to the most. If you go with a Uniden you need to pay extra separately add DMR, NXDN or Provoice so it gets pricey. Honestly DMR is the first one I'd buy myself. Massachusetts still has A LOT of analog to listen to.