You are right, I happened to be in a band that won the WBCN Rumble in 05, and that was Clearchannel connected to the major city wide booking agency. With all the clubs, major acts always needed opening acts, and there was the opportunity (until you became a weekend headliner yourself). The money being made in the Boston area is in Teaching music.Commercial radio also supported local music. It was a really strong scene here until the late 90s when the two commercial stations that supported local music changed hands, one college station went from genre-specific program blocks to “genre blind” programming which meant rock (so the reggae, folk, hiphop, acapella and jazz fusion shows vanished) and an NPR station switched from music to news/talk (axeing classical, jazz, folk and blues). The death of the “alternative” newspaper the Boston Phoenix was another blow.
I’ve been making the same money since I started playing here in the 1980s. What was barely OK money forty years ago is like no money today, I’m lucky if I can cover my travel expenses.
A guy like Warren Senders (acc bass player and teacher of Southern Indian singing) also is "a man with a sign" on Youtube, has students all day everyday, the demand is high. There are other kinds of music that can be earners, like Irish or Greek, or Indian, Caribbean, Fado, Mariachi, etc etc but that's also a wedding band for those ethnicities. Con Salsa is still on wbur 90.9 Saturday night as it was when I lived on Queensberry Street. You can't replace a Tony Cenamo or a Gene Shepherd (both on wbur in those days)
Actually both NPR stations changed formats. I know people who were eliminated from GBH after they built their new complex in Alston (infamous board member) and basically fired a whole generation of producers, went to a Talk Show format (which does support local musicians) as does the new Arts show. WGBH 89.7 has excellent jazz programming these days. They are carrying on from the late Eric Jackson. Unfortunately, Brian O Donovan couldn't be replaced, so Celtic music weekends are now gone from GBH.