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.