I bought my first bootleg LP, "Great White Wonder," almost forty years ago at a head shop on Mass Ave in Cambridge MA, halfway between Harvard and Central Squares. I paid $6 cash, which was a lot. (The head shop is now a store for gamers)
"Great White Wonder" was the first of what would be many Bob Dylan bootlegs to appear (and the first bootleg rock album), and we had all read about it in Rolling Stone -- our newspaper of record. The double LP (which I sold on eBay a few years ago for $125) was a collection of live performances and basement tape stuff with The Band. I bought three copies -- one for myself and copies for two of my co-workers at a bookstore on Boylston Street in the Back Bay. The trip and purchase ate up my lunch hour and my lunch money for the week, but the album was selling out everywhere and we had to have it.
The sound quality was pretty good, and there was something exhilirating about the whole experience of acquiring it -- sort of like early Napster.
I was thinking about this the other day, while listening to my second bootleg recording -- "The Rolling Stones Big Bang Boston 08-21-05," which captures the entire opening night concert at Fenway Park, one of the best concerts I've ever attended. The recording is pretty good, considering that it was captured surreptitiously from somewhere in the audience that night.
I bought it on eBay for $9 with PayPal -- a process that was less exhilirating but a whole lot more convenient.