Hey Hot n Cold, how exactly are you doing the Ultimate Challenge? Because I think I'm doing something quite similar to you. I've always wanted to complete every challenge PC had to offer, but I'm not quite sure how specific I want to be.
For instance, with monotypes, clearly I want to do an Ultimate for every type.
For challenges such as the Smeargle Hunt, I'm planning on doing every color on every generation. (At least I get credit for doing the RBY Black when I solo with Snorlax).
However, for Challenges such as Duo, I don't think it makes sense to do every possible pairing. I think one per gen is enough.
For solos, I'm doing it by family, not each and every Pokemon. Also, I'm just planning on doing it in the first game the Pokemon is available in. However, I'll do at least one Ultimate just so I can get that title.
I'm also not touching B/W. I can't play those games for more than 5 minutes without falling asleep. I honestly don't know why, I guess I just have to have a speed button for it. Maybe a suitable one will come out by the time I finish all these other challenges.
Here's what my list sort of looks like...
Myrrh's Ultimate Challenge List:
All in all, 101/558
What do you guys think?