I listened to the Live Phish Vol. 11 (from 97 I think), a NYE show from 95, sampled some studio stuff (don't like it as much but Joy is kinda growing on me), and jumped ahead and watched a NYE show from 2011. There are still massive gaps in eras I haven't even begun to dig into, but I have loved pretty much everything so far. Don't know what held me back so long
That all said, there's still an intense amount of stuff I haven't even scratched the surface at. I don't know that'll I be going super super deep into their massive catalog, but picking and choosing live shows is working out well so far. Also they are live streaming an audience free show this New Year's Eve for free so that's perfect timing. I haven't listened to the newest version of them, 2011 is the most recent.