i would have fully agreed w/ you anon up until a year ago. i now think the dead is one of the greatest bands of all time, made up of some of the most creative musicians in rock n roll
after getting my wisdom teeth out i was bedridden for a few days and i decided to watch the Dead documentary series on amazon, seeing as I was always told to listen to the Dead but never really got into them. it really contextualized them and their importance in music both at the time and in music history.
i know its cliche'd to make a drug analogy, but as with acid and tripping, you kind of have to let go of pretence with the Dead - you have to ignore how hokey they are, how uncool they come off and the annoying nature of some of their more outspoken fans, and embrace the kind vibes they emit. you gotta really realize that, especially in their live shows, these are 7 - 10 musicians that are at the top of their fucken GAME, and have spent years and years practicing, playing, and experimenting together, and that would go out every night not knowing where their music would take them. they were pure experimentalists, which doesn't really come across in their studio output, and takes time to realize in their live output.
and remember: no band is for everyone. just because a bunch of fucken people like em, doesn't mean you should too. but understand that their appeal often gets muddled in how people express themselves when talking about the Dead, and that everyone's understanding of them is personal and different - so maybe you just gotta find yours.
if you're looking for some essential listening, American Beauty is probably their most recommendable album, and has some killer songwriting on it. as for live albums, Europe 72' has a great mix of reimagined studio tracks as well as some of the best versions of their live-only songs. another great live recording is their 5/8/77 show at Cornell - a great idea of what a full Dead show at their peak sounds like. good luck, be kind