As a veteran, from Kanto through Hoenn, I think I can come up with a reason.
The first games took a forumla that hardcore gamers and little kids could play and appreciate. The game had a certain 'character', a 'charm' if you will, that made it popular.
The Johto games were sort of fan-oriented. It brought new features to the game, but remixxed old ones too. Like FF7 is to Final Fantasy Fans, Johto was to us Pokemon fans. Some say the inclusion of Johto and Kanto bogged it down, but fans loved it.
Hoenn just, well, was fun, but lost its charm. They left out the Day/Night cycle (well, it was there, but for Eveelutions and Shoal Cave), some of the Pokemon were unoriginal (Butterfree - Beautifly, Kingler - Crawdaunt, Gyrados - Milotic, granted a few changes, like type), and its just didnt have the zing the other games had, despite being great games (the games were good, no doubt, but could have been better). A lot of things did change for the better this generation though.
FireRed and LeafGreen remade the Kanto games (besides Yellow) for the GBA, and fixxed the glitches that plagued the game. Due to certain additions, it seemed more bogged down gameplay wise - They held your hand through the game, until the extra stuff, which kicks your ass if you dont use Ubers (which isnt really fun, using Ubers). Still fun, but it was just too easy.
Diamond and Pearl are taking the charm of the first two games, taking the best features from the last three generations of game, implementing things that push the DS to its limit, and are delivering a great game. Its coming back with a charm, a finess, that could easily recreate a phinominom. Its hard to explain how they do it. But there pumping life into a franchise so that it will appeal to more then its already huge fanbase.
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