While I enjoyed Dave's World both during its original airing and on DVD, it is incredibly dated. In the first five minutes of the pilot episode, the characters mention Lamb Chop, Smurfs (a cartoon brought up many times in the series), Ninja Turtles and Barney. This isn't bad; it just dates it pretty firmly.
Most episodes involve Dave trying to figure out what his next column will be. Dave grabs inspiration from his daily life and his interactions with his wife, Beth (DeLane Matthews), kids, and best friends Shel (Meshach Taylor) and Kenny (Shadoe Stevens) and the comedy that typically follows their lives.
During this season, Dave will help his kids understand death when one of them brings home the class frog, but it dies while on their watch. Beth juggles the idea of going back to teaching full time, now that their youngest kid is getting a little older and Shel tries to get over his recent divorce.
The First Season also includes a two-part Christmas episode called "I Saw Mommy Kicking Santa Claus," where Dave has to retake a driving test because his license is 2-years expired, but doesn't pass when he gets caught cheating. Meanwhile, Dave and Beth are looking for the latest hot toy (Cannibal Caveman). But when Dave gets mistaken for shoplifting, their mall experience goes from bad to worse, especially since he doesn't have any ID.
Other good episodes include the cast trying to go to Disney World, or when Shel sells his house and moves into a boat. But this is just a small sample of the various issues that the Barry household will go through in the show's initial season.
If you followed this series when it first aired, or just like Harry Anderson's work, then Dave's World would probably be a good investment. While the series only lasted a few seasons, it still had a good bit of standard 90's humor.