I hate to say it, but Boston radio (specifically from my area) just doesn't appeal to me anymore. I can't think of a personality who I find interesting enough to whom I want to be loyal. I don't like the idea of continuous sports talk. The music stations play music that I can find everywhere else...on demand. HD Radio at least used to have some interesting formats. My personals were back when WBOS had Local 92.9, WROR had the 70s, WWBX had the 80s, and more specifically WZLX had Radio Mojo. I even like WAAF's live music format. But these companies messed up HD the same way they messed FM band (just my non-professional opinion: take it for what it's worth, mostly nothing).
I've gone the road of bluetooth FM transmitter and 87.9 to broadcast podcasts and music from my phone. I don't really mess with anyone, has a FCC regulated range and as far as I know there's not a licensed broadcast on 88.1 in my area, and we have no LPs in the area using channel 6 (87.7).
With that said, I personally use my arra college stations from time to time to find underground music. Thats the big issue.
We used to go to the radio to find new music. Now it's the same repeated artist (not even musicians anymore) over and over. I'm still waiting for a true Hip-Hop station that isn't a pirate. The closest thing to non-cookie cutter radio is the college stations. Without them, it's my little transmitter and XM music in my house through my satellite TV service.