to answer the question if bob really can pull through this:
no. unfortunately not.
the very first obstacle is already impossible to clear for him and his mirror image.
and me.
because you mentioned that this is your first game jam entry:
I can imagine that you mastered a jump combination to get both bobs to the first flag and that it is fun for you to execute, but you should never forget that what feels adequately challenging for you as the developer is WAY too hard for a new player.