Woah, that's a big post.
Can't say I have nearly as much of a nostalgia factor for the series, though I did like it very much for a small period of time, when I last played it 15 years ago. Only ever owned Pokemon Blue, and even then, my 11 year old self was a min-max'y type of gamer (I'm a math nerd), so once I discovered how ridiculously OP Psychic type was (Alakazam, hello), I got bored pretty quick. My bros / friends moved on to other stuff rather quickly (HoMM3 came out around then). While I enjoyed it, it was still just a fad for us, like Yo-Yo's and Tech Decks back in the day (Ha!)
Glad to have rediscovered the series, a decade and a half later, though. I must admit, I always assumed it was somewhat of a child's game due to how unbalanced the first was, on top of its "kiddy" reputation, so I always ignored it. I was never a big fan of the story, either (even now, the 3000 year old story thing made me cringe). But I'm surprised at not only how deep (competitively) the game is, but how much freggin content there is. Also, as I'm more mature, I can appreciate the game's charm much more so than my younger years (near the age when we obsess over being "cool").
The series has really grown immensely since its first installment. The amount of stuff you get to play with, for just $40, is insane. I doubt I'll be missing any Pokemon games in the future.
edit: Wanted to mention that I feel like an idiot for not having "discovered" this series for so long. The game has gotten so big so it's a little tough for newcomers, it's like having to learn DoTA or something from scratch, eesh!