One aspect of this show which tends to date it:
And no, it isn't the fact that it takes place in the 1990's.
What bothers me when I watch the show today is how despite the fact that "Sanders" was instrumental in destroying many of the traditional sitcom tropes that came before it, it also had a tendency to succumb to them as well. One Season 5 episode ends with Hank facing serious legal jeopardy over some Cuban cigars, yet once the episode ends, the cigars are never mentioned again.
These days, we expect our sitcoms to have character and story arcs, and even though "Sanders" is one of the shows that truly transformed the sitcom genre, I get the sense that younger viewers, watching with modern expectations, have trouble sensing just how revolutionary the show was. I know that I certainly find the show's low budget and occasionally wobbly production values far more noticeable now than I did at the time.
But the real problem I now have with the show--and don't get me wrong, I still feel it remains one of the most brilliant in TV history--is the lack of continuity from one episode to the next. As has been noted on these threads, as well as by Shandling and others producing the show, the broadcast order of the episodes was apparently determined after the entire season had been filmed. For example, one of the final shows to air on HBO, "Beverly's Secret", was actually the first episode filmed for the show's final season. First-time viewers watching the show in broadcast order are likely to be confused about why this episode fails to acknowledge the season-long arc (that the show-within-a-show is in the process of finishing its run), yet viewers watching the show in production order would no doubt wonder why Beverly's titular secret--SPOILER ALERT: her pregnancy--is immediately and completely forgotten in each of the subsequent ten episodes.
Is this a fair criticism?