It's weirder that they're as widely hated as they are when their music is the kind of stuff that you'd assume these people would like. It's more the fact that they achieved their success through non-conventional methods and some people have resentment for that. Plus the band's fandom got a negative reaction largely because they had a fandom at all. that was something pretty unusual back at the time, but seems less weird now that every freaking thing on the planet has a weird internet fandom. And while they certainly have their problems, compared to most fandoms out there Phish's fans are pretty chill. Getting into the band has such a high bar to pass that it's only natural that the fanbase can seem a bit off-putting for outsiders.
The "culture" around the band has a lot in common with the dead. It's actually kind of fascinating around their shows with how prominent Dead-stuff still is. Every where you go on the Phish lot there's about as much Dead-related stuff as there is Phish stuff. Dead music blasts from speakers all over the place, and Phish have their own "shakedown street" where hippies sell random shit.
but yeah Phish sounds very little like the Dead at all in the actual music. With a couple exceptions perhaps ("Meatstick" kinda sounds like a parody of "Fire On The Mountain". they also did covers on a few very rare occasions. and of course there's Trey joining the Dead for those 50th anniversary shows, that was pretty cool.)
Phish's studio albums are all good. I think they're good to listen to for people wanting to sample the bands music. The shows are just the main focus and eventually it just kind of sounds weird to listen to studio Phish. Plus tons of their best songs arent on albums anyway.
He talked about how Phish fans treat Phish like baseball, and that is totally accurate with how obsessed fans are with setlists and statistics. But I would go even further and say that Phish are practically Sports Entertainment with how people react to and discuss shows, and the similarities continue into how the band spreads their music too (with pay-per-views, special annual events, media distribution networks devoted solely to them).
He made a good case for The Eagles.
I didn't know about the Springsteen stuff either. That changed my perspective of Bruce a fair bit.