Thanks for starting this thread, I've enjoyed it!
The Dead have had a huge impact on my relationship with audio. I was a mid-80s central time zone high school kid at the record store in the mall, where I was expecting to buy a Cars or Van Halen album. Somehow, I walked out of the store with What a Long Strange Trip It's Been. At that point, the only thing I knew about the Dead was that their fans followed them around and saw show after show. I guess I wanted to know what that was about.
It took a couple years for it to completely win me over, but it did. That album turned into the soundtrack of every late night solo drive, and then I discovered bootleg cassettes. I think the two Americana albums (Workingman's Dead and American Beauty) are extremely well done, but in general, even a crap recording on a wobbly cassette of a live show was better than their other records. I moved far enough east for grad school to actually attend a few shows - the first was April Fool's Day 1990 at the Omni in Atlanta. I was hooked, and started really trading cassettes to build a collection.
Cassettes were the most economical format ever...and possibly the lowest sound quality. Age and frequent use really can make an already-sketchy recording sound like shite. Sometime in the mid (late?) 90s, I found out that people were trading digital copies on cd-rom. I'd never seen a need for me to have a computer before, but I learned how to build a PC specifically to score dead shows and started trading by mail. I ended up with maybe 120 shows, and that's enough...until somebody starts talking about another one I need to hear. I love anything 1968-1978, still have affection for 1979-85 or so, and only listen to anything from the last ten years on rare occasions.
So the first music I digitized and stored as bits on a drive and not on shiny discs was my Grateful Dead collection. Now the shiny discs are just backups for everything, but the Dead led the way.
I might go a month listening to everything BUT the Dead. But then I always want to hear a certain show (2/15/73 just turned 50, and is well worth a listen!) and get pulled back into the van. And when I do, I don't want to hear a song, or an album - I want to hear a show, from start to encore. That's why I still listen primarily to my own (1500 albums plus the bootlegs) collection via Roon instead of just streaming. You can't just stream 4/17/71 when you need some Pigpen, you have to own it. So that's still how I listen to music. If it weren't for the bootlegs, I'd have probably given up "owning" media by now.
I saw about 20 shows, but never saw one at Deer Creek in Noblesville, Indiana outside Indianapolis. So, I've got tickets to "the dead's" last tour this summer there with two of the guys I saw that first show with back in 1990. Just take one...just take one...just take one...just take one...