Gen 2 My Heartgold run!

wise decision! Heartgold is very cool,so cool that i cant describe
btw i dare you to play the whole game without using the starter
(well you can use it to get pokeballs than go get an another Pokémon and just left the starter in a PC , that kind of route is very interesting!)
not saying about nuzlocke

 

maybe do a randomizer or egglock i really like those two challenges its fun to see what Pokémon you have in your team at the end

 

i recommend a randomizer nuzlocke, and if you have a friend you can do a soul link, those are always fun. with the shiny clause and revive clause. I'm personally doing a shiny badge quest for soul silver so im doing a patient challenge thing

 

i also really love gen 4 games because i started playing Pokémon with Platinum version and then my second game was soul silver

 

also if you need a way to randomizer i can give you a link to the randomizer i use for gens 1 through 5 on emulators
https://pokehacks.dabomstew.com/randomizer/

 

You can try the game using just a single type of Pokémon. Like only using water, or fire, or electric. I've been playing Pokémon Ruby like that lately.

 

oh so like a ghostlocke, firelocke, or etc

 

I would say don't do a challenge run the first time through so you get the full experience of the game, but if you want to do a challenge I'd say Nuzlocke

 

Oh wow... I wasn't ready for this.... I didn't even prepare my speech (jk lol)

Another piece of advice/things to know. Pokémon that weren't useful in Gen 2 have gotten a lot better thanks to additional moves and evolutions. So definitely try them out if you can