I just started watching the Pokemon Best Wishes series (based on the Black and White games) and I have the intense urge to watch every episode of Pokemon, so I worked out a system.

1. Get up to date on english subbed BW episodes, there aren't too many so it should be easy
2. In between BW updates, finish the original series (I've seen most of it because I bought a ton of vhs tapes from the video store)
3. Go from there. Orange Islands, Johto, Hoenn, the Battle Frontier thing, and Sinnoh. Obviously skipping episodes I've seen unless I really liked them (like the episodes with Harley, he's awesome!)

I also have the BW english theme stuck in my head (better than the Japanese opening imo). I even wrote the best part on my arm "It's not always blaaack aand whiitee~" I love that part. Ties into N's whole seperation of pokemon and people dealy-o in the games (idk if he'll show up in the show)