I loved the Pokemon show when I was younger, but watching them now... ugh. It's pretty clear that after (and at times during) the first season, their opinion of their watchers dropped like a stone. It got a little better, I discovered, during the whole Diamond/Pearl thing, in which the gym leader fights became whole episodes worth of material, where strategy and reading your opponent actually mattered more than in the games. As soon as that insufferable little hat-wearing twerp gets back out though, it's back to getting lost constantly and not catching any Pokemon let alone do something worthwhile. I don't hate Ash, really, it's just... do something productive sometime, will you, kid?
My retrospective return to Digimon? Whoa man, that show was DARK. Not blood and guts dark, but the kind of dark kids would understand... feeling misunderstood, getting into fights, losing friends and feeling like everything depended on you whether you were ready for it or not. The... ugh, I have to say it... "Digidestined" were just kids, thrust into a situation where they and their counterpart creatures are in constant danger. They get beat up, they had to watch friends die, they had to hoof it across an entire continent, and they had to face incarnations of evil itself, whether it be obsessive evil, mindless destructive evil, selfish acquisition evil, desperate evil or just sadistic, calculated evil... those kids had to face it and survive.
Summary: Pokemon Season 1 and select episodes are okay. Digimon Seasons 1, 2 and the movie were fantastic and still stand among the great anime series totally on their own.