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My first thought was Whitney but after thinking it over, I realized I don't hate her but just that Miltank of hers. The gym leader I hate most is Clair because she's a sore loser and makes you go on a really pointless side quest before she'll give you the badge.
It'd either have to be Rayquaza or Registeel. I say Rayquaza because it's green (my favorite color) and also the first dragon type legendary. The reason I like Registeel is because...well it's a robot, golem thing and has a really epic cry.
I really like the Battle Pyramid as it's the closest thing to an overly difficult challenge I've ever experienced in a Pokemon game and when I finally beat it, it gave me a really nice sense of accomplishment.
I never plan my team the first time I play through a game because I like wandering into the unknown and catching and using whatever Pokemon seem interesting to me.
Usually by the time I go to the Sevi Islands for the first time I'll have my whole team. As late as I can remember going without a full team is right before the e4 when i caught and used an Articuno.
I don't think I'll stop entirely but it'll be some time before I pick up a gen 4 game again. I've completed the national dex and mostly everything else on all of them (except soul silver) so for the time being, I won't be playing them.
I really like all of the Team Aqua and Magma trainers. I think they are the most well designed evil organizations as well as having really epic battle themes.
I would always go with the acro bike because I find it way more versatile and easier to control. I only switch to the mach bike when I absolutely have to.
I'd rather wander into the unknown and play a game without a guide. I rarely get stuck in Pokemon games and when I do, I eventually find my way. I've never bought one and have never been tempted to.