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Mostly it grows over time. Gen I/II were the peak and then Gen III came and pretty much destroyed the fanbase. Seriously, you can see old ancient internet posts from people who are acting like they are with this game (and I'm one of said people not looking forward to LGPE, but I love the shit out of Gen III) because they removed the option to transfer old Pokes and rebooted the franchise with a new roster, with lower mon count than Gen II. But then it actually have all 386 Pokemon in the code and FRLG came to allow for a full national dex, which led to it getting some more steam but I argue it wasn't until DP came that more folks got into the series after that backlash, due to the online/Pokemon transfers being established.
I think BW was where this whole fear in GF of appealing to lapsed players came into play, since I vividly remember a lot of stubborn people being pissed by the lack of any pre-Gen V mons in the main story, and some people went on and on about the designs of the new mons. Ever since, I feel GF has been trying to win back the Genwunner crowd in any way possible, either in good ways to make everyone excited (Battle Tree/PWT) or awful pandering ways. (XY Kanto mons, Alolan Forms) That worked with XY and SM both as they brought back a ton of lapsed folks, and SM in particular came out after the Go boom which lead to it selling super well. So pretty much every game sans Gen V has tried to appeal to new players, lapsed players and longtime fans, while BW was more or less meant for new and old folks.