I hear ya Steve. It happens to every generation, but I have to say the boomer generation (to which I belong, as did Petty) for some reason thought it was the exception to the rule---a Peter Pan fantasy.
While living in L.A., I met and became acquainted with, amongst other artists, Billy Swan (writer of the hit song "I Can Help"). He was a Southern boy, who told me about seeing Elvis live in ’56, performing on the back of a flatbed truck at a County Fair in Tennessee. What I would give to have witnessed that! I suddenly understood why the younger musicians I was meeting were so envious of my saving seen Hendrix, Cream, and The Who (with Keith Moon) live in the late 60’s.
Everyone thinks of Rock Stars as living easy, cushy lives. But Petty was unusually fortunate---most artists of his type live in abject poverty their entire lives. I met and became acquainted with the guys in Dwight Twilley’s band, after drummer Phil Seymour left for a solo career. The Dwight Twilley Band’s debut album (Sincerely---a fantastic album) was partly responsible for Mudcrutch leaving Florida for L.A. in search of a record contract. Twilley hooked Petty up with Shelter Records and, as they say, the rest is history. Anyway, the guys in Twilley’s band were living on $150/wk each in 1979/80, which didn’t go far in L.A. (or anywhere else). THAT is the reality for most musicians. Dwight himself, at the time living with Susan Cowsill (yeah, those Cowsills), was doing only a little better than his band. He watched as his admirer Petty, for some reason, stole his thunder, enjoying a very successful career, while he languished in relative obscurity.
On the other hand, Petty is dead, and Twilley lives on!