You can really start anywhere. The problem is, if you haven't been following since the first couple of gens, you might find the later games a bit overwhelming. Mainly because there's just too much fucking stuff to remember if you want to do anything other than play casual.
I'd suggest grabbing Heart Gold/Soul Silver, or Black 1/White 1 since they're the most recent and I can assure you they're good. Try to avoid Diamond and Pearl like the plague. I haven't played Platinum, but I heard it was a significant improvement on Diamond/Pearl, and I haven't heard really anything about Black 2/White 2. I don't ever plan on getting B2/W2 either because it looked like it was just B1/W1 except with a different story and slightly altered region. When it comes to Pokemon, I have no interest in the story.
You could wait for X/Y, but we have so little information on it right now there's no telling how good the final product is going to be. The first generation is complete shit, so I only suggest playing it if you just want to experience the originals.
Oh, and as far as which version of the gen to pick, just look up the version exclusives. Most of the time the only differences are the Pokemon, but in B/W's case there are entire sections of the game that are different.
E-Hahahaha pirating a pokemon game dude just go snag roms of every game up til gen 4 you can find them so easily
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