My standards for how to enjoy each Gen.
>Gen 1
Perfect for glitching out and having fun with busted mechanics for a laugh. It's really short, so this works well. Bonus points if uploaded to Stadium to blitz all the challenges.
>Gen 2
Sadly, these games do not have anything going for them. The music is great though. Just play the remakes for a good Johto experience. Stadium 2 is a treat.
>Gen 3
I only play this gen with friends. Use a hacked Wii to save edit some cool 'mons and use them in Gale of Darkness battles via GBA link and have some tournaments. Doubles Gen 3 is fucking fun.
>Gen 4
This is THE go-to gen for the Battle Frontier. Plus, with the aforementioned hacked Wii, Battle Revolution fun.
>Gen 5
No side games to support anything interesting so the only real enjoyment is the sequel games World Tournament and the Battle Sub.
>Gen 6-6.5-7-7-8
Each respective game's online play. Replaying these games is a big no as the slogfest the main campaigns have become makes enjoying relays impossible.
>You can't just skip Gen 2!
Only play Gen 2 with Stadium 2. The main game's problems are mitigated by using the Gameboy titles to build random teams to put through the challenges.
>No side games? That's a bull shit reason for Gen 5.
It is, but with how long the games have been out and all of the supporting content that made it special is all shut down. No reason to go back.