Very interesting take! I will say that since around 2003/2004 I've personally felt Pokemon has started to slip a little. I still love the games and play all of them but I have noticed the stagnation and struggles. Maybe the change in leadership did have an effect? Hard to say without having worked their since around that time ya know? Still, from the outside looking in, we're just theorizing.
Shame I've heard such terrible things about Little Town Hero. I thought it looked interesting when it was first shown but it seems to have a lot of issues. I don't think it's very beautiful either like some people do here. It looks pretty bleak. I wanted this to be great, but with too many games coming out this season I can't afford to buy them all.
Apparently Satoshi actually only directed up to the OG Pokemon 2 before it's current overhaul with Masuda taking over from that final version. Masuda directed Ruby and Sapphire and onward, so I was a bit wrong.
I adored the main 3rd gen games. Fire Red and Leaf Green were more off because of the difference in key for the majority of music which never made sense to me. The actual faithful remixes were amazing.
But Diamond & Pearl were the first to feel off to me. The hype cycle was incredible. We had over two years of teases and they were very smart to sprinkle the first new Pokemon like Munchlax and Lucario into 3rd gen movies, with Munchlax making his debut in Destiny Deoxys in 2004, which was only the 2nd film of that gen. They kept the hype going for years with infrequent but just enough Coro Coro teases and reveals. This was never replicated and is one horrific misfire by TPC since that's their role I'd think; marketing.
But the pay off was lacklustre. I can't put it into words but DP just couldn't hold on to my attention. Might have something to do with such a abysmal side-game period. Battle Revolution was a rushed, shockingly unpolished mess (oh that slow down when Submission was used... oh god). Without console games to keep the feeling alive, that was missed. Plus the anime was still reeling from the very controversial voice cast change (and this was still the Taj era), that hurt a lot also.
Platinum was the first 3rd version I skipped, and I only got Soul Silver back in 2012... only to sell it without even cracking it open. Diamond to this day still hasn't been played much and to this day I've yet to play a Pokemon game to the very end. Emerald and XD hold the honor of being my last completed Pokemon games.
This isn't an age issue since Pokemon still is one of my fav franchises period. But I guess I'm just in that seemingly never-ending rut and just seeing the serious flaws and just hold onto too much nostalgia for the first three gens? I dunno.
Actually it just occurred to me that they made an extremely critical flaw; they didn't bundle Pokemon Box with Colosseum. This would've given people a much more Stadium-esc experience. Hell you can see a lot of resemblance to Oak's Lab in the Stadium series in the interface and art assets. Hell Kenta Nagata from EPD returned from Stadium 1 to co-compose that game.
Something like that in the 4th gen could've been crucial. A proper follow-up to the Orre games by Genius Sonority (had they not been horrifically down-sized in 2008), plus a successor to Pokemon Box (not Ranch, or hell, use Ranch) bundled with the game to have DS playback (with the DS itself still using touch if needed) on your TV, that could've been huge.
The franchise's absence from home consoles pre-Switch in terms of RPGs was a serious void in the franchise. Might've helped Game Freak be more prepared for 3D themselves maybe as well.
That's my two cents anyway. :P