You've got a lot of guts, Adam. I can't even watch a show I hate on tv and that's free, let alone spend hard earned money on a season set of a show I hate.
I have blind bought many shows on DVD though and there were a few I didn't really care for.
I used to love JSM when it was still on the air. I sorta lost interest in it after watching it so much when it went into syndication, however. I'm not sure if I'd ever buy it on DVD. The 3rd season is when the show really started to take off, IMO. I don't know if you were aware of this, but Joe Rogan, Stephen Root, Andy Dick, and Dave Foley all appeared on this show.
In fact, the episodes with Dave and Andy were among my favorites.