PokéBase - Pokémon Q&A
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I haven't had the games for a few years but im gettin back in the pokemon circuit. im an old school poke veteran (super nerd i know lol) and ive accomplished this before, however you will need multiple older generation games, 2 game boy advances with trading cables, a ds, and of course the newer generation game(s) of your choice. Its not cheap, easy, or by any means quick, but yes, from the first generation you can (through a process) trade all the way up to Black/White: first, from red version, trade to gold/silver version on 2 gba's; from gold or silver trade to ruby/sapphire; from r/s migrate to diamond/pearl/platinum; then finally on to black/white.

i guess my question then, is can anyone help me find an easier way? i got a job and a house n im all growed up, but i get some free time when my wife's with my kid, n i plan on eventually owning every version.

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Well, actually you can't trade form Gold/Silver to Ruby/Sapphire because In Ruby/Sappire, they introduced a IV and EV system which would totally screw the system up if you could trade from those two games. But you can play Fire red/ Leaf green for the pokemon. Even Bulbapedia says so.

http://bulbapedia.bulbagarden.net/wiki/Pokémon_Gold_and_Silver_Versions#Connectivity

The games are not compatible with games released as part of later generations.

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Are you sure? You've tried trading from G/S to R/S? Because I'm certain I've done it before. What happens is you simply can't attempt to cross-trade pokemon with any new-gen. moves or held items (e.g., you'd have to trade old gen pkmn with old moves from the new gen game to the old one for it to work), but this does work. I don't mean to sound rude...i was just asking if anyone knew an easier way but i suppose this is the ONLY way..
Yeah then, I'm pretty sure that that is the ONLY way. But I'm 100% sure that you can't trade to R/S
Why was this voted down? It's a perfectly good answer, and the right one as well