WOW, what a great question.
As a guy also devoted to live music in venues large and small this is not an easy question for me to answer.
I have forgotten more live music shows than I can remember. I have seen Sinatra, Elvis, AC/DC, Pink Floyd (early and The Wall tour), Bob Dylan, The Stones (several times)..... Zappa at the Uptown previously mentioned and a whole lot of shows at the Grand Emporium. Sorry the fingers kinda took off on their own.......
My all time favorite memory is being a teen-age, white kid with a date going to a Parliament/Funkadelic show in Birmingham Alabama in the late 1970's. When the space ship landed the place went wild....... For a live show at a large arena, that has been the yard-stick that I have measured against for 40 years.
Again great thread ......
PS- my uncle was last at Woodstock for about a week told me to save all my ticket stubs. And I have about 3 coffee cans filled with stubs in envelopes sorted by year. My kids seemed to look at me differently when I showed them the stubs.