>>56955596I'm talking about Smogon and Random Battles because I play those the most. From best to worst:
The best (8/10 or better experiences)
>Gen 4>Gen 3>Gen 6POWER GAP
The middle (6 or 7/10 experiences)
>Gen 2>Gen 7>Gen 5POWER GAP
Good to try sometimes (4 or 5/10)
>Gen 9>Gen 1POWER GAP
Buttcheeks (3/10 or lower)
>Gen 8The top 3 in my eyes are the best meta with the split (also best without team preview, best overall, and most accessible with fundamentals), the best pre-split meta, and the best team preview meta. Gens 2, 5, and 7 are all fun in small doses for very different reasons. 2 is super slow and methodical, 5 is the only one with true weather wars and pre-nerf Hidden Power, and 7 is fucking chaos. They work best as a supplement to the top 3 in my opinion, but I would rarely choose to play any of them. It gets more nuanced if you look at tiers below OU. Gen 9 is interesting, I just think it's marred by some of the worst balancing ever. Tera is cool and every decision matters. Gen 1 just a mess, but at least it's straightforward. Gen 8 is absolutely robbed by its lack of an interesting mechanic to set it apart, really slow gameplay, and bad balance. It's like playing Gen 4 with absolutely none of the enjoyment.
All of these numbers change if you're playing Battle Spot or VGC. Gen 6 is probably the best on cart for both of those in my opinion. It's relatively easy to build a team on cart, nothing stands out as super unbeatable, Megas are a reasonable gimmick without Z Moves to worry about, and bullshit introduced in Gen 7 is absent. It's the only Gen where I really didn't enjoy the story, but found the online to be enjoyable on cart.