I went full autism and counted up all the Pokemon I love from each Gen and worked out the % of the Dex I really liked (includes regional forms, but not Megas).
My the overall rating came to:
3 > 4 > 1 = 8 > 2 > 5 = 6 > 7
>Gen 1: 45%
Nothing really surprising here, Kantooo has a ton of solid designs.
>Gen 2: 43%
Right in the middle suits the least memorable region quite well tbqh
>Gen 3: 67%
No surprises here, the GOAT dex
>Gen 4: 54%
Surprised this one was so high since I usually think Sinnoh is kinda forgettable. I guess the reason is because most of the Pokemon variety is locked behind gimmicks so you never get at the cool shit. And the number of cross-gens means it never really feels like you're using Sinnoh natives.
>Gen 5: 41%
Probably the biggest surprise, I probably would have listed this as my favourite generation for designs before. I think the problem is while Unova has, imo, some of the best Pokemon designs in the series, most of them have really shitty prevos which deflates the count (Haxorus, Chandelure, Excadrill, Seismitoad, Conkeldurr, Elektross, Volcarona, Hydreigon all spring to mind). Also a lot of LegendariesI don't like doesn't help the %.
>Gen 6: 41%
No surprise here either. I think a few from this Gen are excellent but most are pretty boring.
>Gen 7: 40%
I actually like this Gen's designs a lot, but the absurd amount of terrible Legendaries/UBs hits the % hard.
>Gen 8: 45%
I actually like quite a lot from this new Gen, but the complete lack of Legendaries for me to hate is probably inflating the count.
I thought this would be interesting to try but I don't think it's really the most representative. As someone who doesn't like many Legendaries, the count pretty much came down to them. The only Gens I'd say I like the Legends from are 1, 3 and 4, and they were the ones that came out on top, with 8 matching because it doesn't have any.
I might try it again and discount them to get a better judgement.