Position from which I have the worst escapes: Probably also going with north/south bottom. (Turtled up is also high up there, but I’m getting slightly better about at least flopping towards half-guard. But I’ll save that for round 2 of this assignment.)
New Escape: …I’m terribly unoriginal right now, aren’t I? The spider guard thing Josh described is one of those that I would love to be able to do, but which would “never” work for me. North/south escapes in general “never” work for me because guys clamp their elbows to my ribs better than I can create space. My usual attempts to escape are just me being as wiggly as possible until they decide to transition to something else.
Now if it were nogi, that isn’t as useful. I guess I’ve got the flip over the back, which I never even go for since it’s difficult on body mechanics alone (that is, I have short legs, so I can’t always get all the way to the back) and I’ve never come even remotely close to getting it ever in live rolling. But, the assignment is for something would “never” work.