If there is such a thing as an overrated show, and I tend to think there isn't (except post-show when so many people are clamoring "that's the best show I've ever seen"; no matter what it was like), the first shows that come to mind are The Warlocks shows of October 1989. I'm fully aware of the breakout significance, but beyond novelty and theory, they don't do a ton for me. I loved hearing Dark Star as much as anyone who is a DS devotee, which I am, but there's the cold reality of "yeah, this isn't really all that great" that came with the Dark Stars of '89-'94. I was at Shoreline in '91 when they played it first set for the first time in 1307 shows and teased it a few times in those two days. It's like getting slingshot up K2 at sonic speed and then instantly falling off the top of the world. The peak and satisfaction is almost non-existent. I don't think Jerry was all that subtle about not enjoying playing it anymore.
Wow.. you nailed it on all counts. If there was one pick I struggled the most with it was this one. Lets start with 10/9 ---even though I concur on your Dark Star thoughts catching the breakout at a show billed as "The Warlocks" ..not to mention the first Attics since 72, the first East Coast Death Don't since 1970....deserves the spot. Even though I attended a ton of shows in 89 if I was being honest LOL this is the show I didn't make and regret missing most. I can only imagine the crowd going apeshit and the "special feeling & magic" that must have been in the house. I think this is one of the ones that being THERE was a lot more than what a tape can convey. Damn now you just reminded me of one I left off 4-2-89. for unique reasons also ..time for an edit/addition.