Honestly, it's a bad season because it was rather badly written. It might be because it's pretty much advertising the games and thus there wasn't enough time to produce a proper plot, 4KIDS refused to remain true to the script at times (though they made the Team Rocket trio one of the best characters in the show, I'll give them that), jelly-filled doughnuts, Pikachu the horn, Ash didn't really win all of his badges properly, Brock's mother is "dead", the infamous Porygon episode, there's a lot.
However, even with the bad writing and plotholes, and the blinding nostalgia, I do have a soft spot for it. If anything, I like it for the lulz, and also to see just how much has changed since the beginning. I won't watch it all the time, but if I buy the first season boxset, it'll be for my own kids to watch.