4 > 3 > 5 > 6 > 2 > 1
Platinum best.
>best region
Tied with Hoenn which had variety (volcano, desert, rainforest, ocean) but was significantly smaller. Sinnoh was also super comfy. Unlike most other Pokemon games, all towns stick out and aren't generic.
>best music
This isn't even up for debate
>best difficulty
Set + noitems = you actually have to think while battling
>best metagame
Gen 5 is weather wars and Gen 6 is Priority: The Experience.
Gen 3 is second. Felt like an adventure, great fun and all but I find it hard to go back to it because no physical/special split.
Gen 5: I didn't like Black/White much but I really loved the overall improvements such as reusable TMs and the fantastic new exp curve (why the FUCK did they remove it in X/Y? Why? The new Exp Share is shit). It's fun to play romhacks of this gen.
Gen 6 is fun to play but I don't like the Steel nerf, fairies or Megavolutions.
Gen 2 was absolutely fantastic for its time and ambitious as fuck, but I honestly feel it's aged badly because of the retarded level curve and squished regions. Not even HeartGold and SoulSilver fixed the former.
Gen 1, again, was great and fun for its time but all of its mechanics have aged like milk.