I came up in Boston and played there in the 80s and 90s, mostly original music. I found it tough to make a living just playing in Boston. Once my band started touring, it got a lot easier because we got some respect. Lots of places to play back then, although it seems that most of them are gone. Around the time I left in 1995, the Paradise was my hometown gig.
You are definitely right about no cover band gigs, at least back then. I didn't know anyone who played covers. I did a few GB gigs here and then, but most it was originals.
My first gig ever was at the Rat in 1979.
We probably crossed paths quite a bit. I was in Boston 1974-1994, and started playing the jazz, folk and rock clubs in 1977. Some of the places where I played (Boston, Cambridge, Somerville) were: The Idler; The Blue Parrot; Passim; The 1369 Jazz Club; Michael's Jazz Club; Pooh's Pub; The Channel; Bunratty's; Great Scott; Molly's; Harper's Ferry; The Paradise; Jumping Jack Flash; The Rat; Jack's; Ryles; The Sunflower Cafe; Jonathan Swift's; Johnny D's; Club III; etc., etc. I played on the WERS Sunday afternoon live broadcasts from Passim several times (and did the in-studio show), and appeared on local (New England) television a few times. Once, when I was on a morning show, I went to the donut and coffee table and ran into John Ehrlichman, one of Richard Nixon's henchmen, who was on the show to promote a book. I also played a lot of GB gigs, around 1979-1981, mostly on the North Shore. But yeah-- cover bands were really few and far between.
Boston was a great "training wheels" town, where you could play *a lot* and work on your craft, but the music industry wasn't there. If you met a random person and said that you were a musician, the person might say, "My brother-in-law is a bouncer at Chet's Last Call. Would that connection help you?" After I moved to the NYC area, the analogous person would say, "My next door neighbor is the president of Columbia Records. Would that connection help you?"
I would gulp and stammer, "Thanks! Maybe in a little while!"
There was that brief period when some Boston bands suddenly got major label deals -- Face to Face, New Man, Til Tuesday -- and every other decent original band was salivating. But that didn't last long.
I remember the Boston music scene as being oddly divided between the many music students and teachers, who played jazz, and the locals, who played garage rock (like the Neighborhoods). There wasn't a lot of R&B, blues or country music around there back then.
I was able to survive on gigging for a few years, but largely because I was playing with a singer/songwriter who had an agent who got us lots of college gigs and excellent opening slots out of town, as well as in the Boston area. We toured around the Eastern half of the U.S. for most of the '80s. What killed a lot of that was the drinking age being moved from 18 to 21 in a lot of states. Before that, even the college gigs which were "coffeehouse" things usually had some alcohol around. When the alcohol left, the student activities people spent the money on things other than live music.
Well, this didn't help the OP one bit, but it was fun to reminisce!