There is a combination of research and gameplay that you have to go through to truely master... anything. While I am not sure of the ratio, I know this for certain:
You can learn more about damage from a damage calculator (Or *ahem* the attack/defense tier lists :-p) than you can from playing the game. You can learn a lot more about speed from looking at the speed tier list than playing the game. Etc. etc.
But then of course, you learn more about prediction, surprises and actually playing the more you play. So it is give and take.
One other thing that comes to mind regarding experience: Nethack. Most people here probably don't know what it is or haven't played it -- it's an ASCII graphics dungeon crawling game with elements of D&D (it's a Roguelike game).
My point about it is, Nethack is FILLED with tons of random and unpredictable things, and a multitude of ways to kill yourself by one stupid action. It's incredibly difficult to win the entire game. I'm not great at it, but I still find it difficult even after having played it for years off and on, and read tons of spoilers about all the items/monsters etc. The result: I have (though I forget things) a giant random mental archive of tidbits I've picked up about the game. Someone who just started the game, even someone who'd read a guide or two, would probably never have the sheer amount of knowledge you get from doing/studying it for so long.
It took me only 3 years to ascend biatch! Thank you spoilers! I never would have done it without ya :-p And I got to Medusa in under a year. And hell, I used a Ranger instead of Barbarian/Valk. So yarr...
Nethack is on a tangent because as you said, there are billions of obscure ways to kill yourself. But in all honesty, you learn more from reading the instant-death spoiler than actually doing the instant-death over and over and over. Unlike Pokemon, Nethack
deletes your savefile every time you lose. So unless you are a save scummer (which is essentially cheating IMO even worse than spoiler reading), I'd say reading a guide or two really really helps in Nethack. Even moreso than in Pokemon. Granted, there is an argument that the fun of Nethack doesn't come from winning... because in many ways you are not expected to win but to simply play (or should I say... have the game play with you)
Also, despite us giving off an air of elitism (and yes, some of us are outright elitist), I'd say it's pretty damn necessary. If we weren't uptight about our discussions actually being discussions, we'd regress into the hellhole that is GameFAQS and possibly Serebii as well.
I'd like to publicly state that I disagree on this point. I feel it has more to do with this place's elevated knowledge of Pokemon and less about elitism. That said, the mods run the show in the end so perhaps my comments don't matter... but I'd like to simply disagree :-)
tl;dr: If you think OU is boring, it's usually your own fault and not the metagame's
If he thinks that OU is boring, then he can go ahead and play BL. >.> I hate to raise this into a meta-argument... but he can play the game the way he wants to play it... I mean I agree with your specific points but I don't think we should be arguing about this topic.