Honestly? I think that if Dan had the ability to do whatever he wanted, he could pull this off. As we saw in the livestream, he has some downright cruel ideas about how to design a Mario level, which were only tempered at the time by Jeff's knowing the line between difficult level design and just straight sadism. Without that limitation, he has free reign to do whatever Saw shit he can possibly dream up.

BUT.

I don't think he'll be able to break Patrick. And it has nothing to do with his skill as a level designer, and everything to do with the game itself. As we saw in both live streams, the Giant Bomb levels were pushing the item limits by the time they finished. This means that Dan only has about the same amount of content that he'll be able to put into one level, and I think that just won't be enough. Patrick's been able to triumph over the two community levels already, in much less time than he has for the challenge. There just isn't going to be enough that Dan can add into one level that will up the difficulty enough so that Patrick won't be able to beat it. Ultimately, I think that game limitations is going to be the deciding factor that lets Patrick take this over Dan.