It seems worthwhile to stretch out a bit with some musicians I'm especially interested in (though there are many who aren't here and ought to be...). This is very under construction, will be organized and annotated real soon now...

Making a living as a musician is ...difficult... Few escape the hours of travel away from wherever home is, not much money (or somebody else gets a lot of it), a million lifestyle temptations (drink, drugs, sex), strange hours and bad food, and audiences who expect something (right down to music you may have come to hate because you've played it so many times) and expect you to be at the top of your game, since they've paid to see you. And it's not much better for even high-end classical musicians. Most of the biographies I've read and documentaries I've seen emphasize what an awful life most musicians lead. Consider Clarence White (1944-1973), genius bluegrass guitar innovator, killed by a drunk driver as he was loading his car after a gig... and recollect the deaths of Janis Joplin, Jimmy Hendrix, Hank Williams, Charlie Parker, Billie Holiday, Elvis Presley ... and resolve to read the obituaries of musical luminaries as they die off, often early...

Gillian Welch and David Rawlings nail it:

Nobody had ever seen a white boy move like that.
He was a flesh-and-blood rent in white reality.
A gash in the nature of Western things.
Through him, or through his image,
a whole culture started to pass from its most strictured, fearful years
to our unpredictably fermentive age-- a jangled, discordant feeling,
at once ultra-modern and primitive...
(Greil Marcus, quoting Michael Ventura 1986)

Here's how David Sedaris puts it in the 4 April 2022 New Yorker:
The last show I did before covid-19 robbed me of my livelihood was in Vancouver, British Columbia, in a theatre I didn't much care for, a rock house with a grim, cramped lobby and the sort of dressing room you see in movies about performers who overdose on drugs because their dressing rooms are so depressing. The audience was lovely, though, and I liked my hotel, which, at the end of the day, is really what it's all about. I'm never the one paying for the room, so I'm spared the part where you lie awake and wonder if it's really worth six or seven or eight hundred dollars just so someone can creep in while you're out and arrange a pair of slippers beside your freshly turned-down bed. They're on the carpet and look as if they belong to a wealthy ghost who's just scooted over to make room for you.