After reading through this thread, it's obvious a lot of reasoning behind it being the so called "greatest generation" is nostalgia. Obviously everyone is entitled to their own opinion on the matter, but I see more valid discussion from people going against it, although there is some good reasoning behind both sides. Personally I would put Gen 2 on par with Gen 3 for me. Gen 4 was my favorite, for many reasons but that's not what this thread is about.
Something about G/S/C just feels incomplete, like there could have been so much more done with it. People who say they liked it because of it's superior plot line, but I have to ask why? How is D/P/Pt storyline in any way inferior to it. Team Rocket in Johto just seems like they were put in solely for the fact that there would be more then just Gym battles. G/S/C has been the only game where I felt if I didn't interfere with their plans that the world would be fine, the whole "lol child stopping criminal masterminds while almost no one else does anything" not withstanding. All they did was chop off Slowpoke tails for money, albeit cruel not really all that important, force magikarp to evolve, and try to call their former leader who clearly didn't have any interest in returning based off events from the previous game. The legendaries were not really giving much of a back story, although that has happened recently as well, but only because the absurd amount of legendaries that they keep adding. Ho-oh and Lugia played very little to nothing in the storyline, been a while since I have played G/S/C. The main legendaries in future generations all played a pivotal role in the plot, and actually felt like they mattered as legendaries and weren't just random add for the sake of having them. Crystal added a little story for Suicune, which wasn't all that bad but it didn't really lead up to much. Compared to future generations it just doesn't feel like it was a good storyline, probably even worse then Gen 1, which at least made it seem urgent that team rocket be stopped. People seem to like that Johto was an actual sequel instead of just another new storyline. I don't get the big deal with this. Obviously R/S/E wasn't gonna have anything to do with Kanto and Johto things. It's a totally different place far from it. Johto made sense being connected to Kanto and all, but Team Rocket really didn't do many memorable things that would cause world wide news. D/P/Pt kind of implemented some connection to Johto, but it really seemed pointless and more of way to show that it was happening the same time as Johto, also making it unable to reference R/S/E because it hadn't happened yet.
Another thing people seem to enjoy was being able to revisit Kanto, Honestly to me Kanto just seem to be put in to appeal to people because it was there first pokemon game, and to show people new to the series kind of what happened before. After I beat the Elite four I was extravagant to go back to Kanto and re-challenge all the gyms I had beaten previously, but shortly after beating the first few gyms it just felt like I was only going gym to gym with nothing in between, aside from that lame rocket (did that Power plant thing tie into the story at all? I forget.) Kanto looked like a nuclear war had broken out, Viridian forest, Seafoam island, Mt. Moon, Cinnibar and no safari zone, completely butchered. Even the big ending where we get to fight the character we were in the first game, was probably the biggest disappointment to the ending of a story I have ever seen. What's the big obsession with Red he is such a lame character, he could have been generic Youngster #4156 and it would have been the same lame result of "..."(battle)"...", not even any recognition or congratulations from red, he just becomes a sore loser and disappears forever. Frankly if they would have axed Kanto and just made a little reference to it, and expanded Johto it would have been alot more enjoyable, and increase it's replay value for, me anyways.
While I enjoyed some of the 100 new pokemon, there was just as many stupid pokemon, every generation has it's gems and crappy pokemons. Pokemon like Girafarig, Dunsparce, Corsola, Qwilfish, etc..., the only generation that hasn't been all the spectacular was the 4th generation, but even it had quite a few pokemon that were interesting.
I do have to say the Johto had a lot of things that were superior to the other generations. It had the best rival by far. Blue/Gary was just a generic superiority complex who thought he was better then you no matter what, and it took him until the end of the storyline to have a little character development, if you could call it that. R/S/E had the assistant of the professor as your rival but they were the worst by far, they had a good start going for them put fell apart and removed about halfway through the game. I guess Wally could count but he only makes an appearance near the end, most likely just so the games could kind of remain consistent. Barry wasn't to bad, but he felt more like a friendly rivalry which is kind of boring, although he was probably the funnier rival, he just didn't feel as epic as silver. Silver start off well with stealing pokemon, and although he slowly starts to feel like the lame "I'm the best and your just pathetic" Gary knock off, when he meets lance and slowly starts realizing what it takes to win, he reall starts to develop, while still kind of retaining that cockiness that made us love him in the first place.
Johto also had the most enjoyable music, places like the unown ruins had awesome music. It also implemented many new features, some that are really the staples of today's game. Breeding, Night and Day, Shinies, Female characters and the Battle Tower, to name a few. As well as fixing many problems that R/B/Y had mainly psychic imbalance, the stupid Pokeball system. I can't just see this as a good reason why it's so enjoyable I guess if you played the first games and got frustrated with that kind of thing, I guess. If that's enough to get over the many things wrong with the game, all the better for you, but for people who started with them seems like they got the shaft. Also the metagame sucked hard, Curselax was a whole new level of broken not seen until Garchomp. (Possibly even more)
All in all alot of potential but poorly executed with the technology they had at the time. If it R/S/E and it were switched it probably could have been better, story was lame though, but I guess when you're 10 it doesn't matter much. If Kanto had been ignored it could've have realized it's potential.
Anyway that's just my opinion and if you liked it this shouldn't change any opinion you have, I just feel many have a problem with looking at things with rose colored glasses and don't give a lot of justification other then it was when they were younger and pokemon just felt more exciting back then.
Me and my brother.... I mentioned that earlier in the post...