Ooh! I've never even thought about that! O_O Huh... let me see...
Well, back when I was treated like I shouldn't exist (had a bad childhood) it was one of those games that made me feel like someone. ^^ Even though I couldn't speak English well... (my games were in English so I could learn how to speak it) the thought of exploring a different world, without the abuse from my family and not feeling like an outcast, was amazing to me back then. ^#^ I didn't have any friends when growing up, and later only had people claiming to be it just to steal my stuff, but capturing a Pokémon felt like capturing a friend that would aid me in my quest. ^^ Sure, I couldn't really interact with my Pokémon... but working together as a team and overcoming challenges made me feel happy. =D Whenever I beat a trainer or someone at the gym, I didn't feel like the loser I was in RL. ^^
I suppose it's because of how much I needed the series to help me get distracted from the harsh reality that was my life, and gave my scarred mind some positive thoughts and feelings, even if it was just for short period of time. ^^ I grew quite attached to it, much like many Nintendo games. =)
When the second generation came out, I was so happy that I cried. More Pokémon, more people, a bigger world, and I can actually sort of befriend myself with NPCs! =D I always loved the designs of the Pokémon in generation 2 the most, and the fact it introduced baby Pokémon was adorable. ^^
Generation 3 was quite good too! Nice colorful graphics and more Pokémon. ^u^ Also 2 teams instead of one, wow. =O
The next generations were quite alright, but uh... Pokémon Moon made me afraid for the future installments... Sigh... you know why I loved the first few generations? I loved them because they made me do this on my own. My mother never believed in me, saying I cannot accomplish anything and am an eternal failure. But the game's difficulty and the lack of assistance made me feel like I wasn't that. =) Now however... being lead by a professor, Lillie and Hau in my journey... I felt like I was being belittled. ._. Even with a language barrier could I beat the games. Why does it insist in preventing me from exploring the world and forcing me to stay on a path? Let me explore! Let me feel independent! Don't force me to listen to your expositions and conversations, forcing me to stop my progress only to try skipping hours worth of dialogue throughout the game. ._.
I'm sad to say, but I may quit the series if it's going to be like Mario Party 9, changing the things I used to love. ._.
So um... is that a good enough answer? ^^ Or should I add more? =O