Ordering by average perceived difficulty won't solve the problem as different new readers will have very different backgrounds - one might find mathy post A easy and psychology post B impenetrable, while the next guy votes the opposite.

Maybe posters could be encouraged to watch out for illusion of transparency and clearly signpost to the next step back on the inferential distance tree, and commenters to suggest such links where the posters forget. I could always figure out what OB posts were about by following these links (whether to other OB posts or not) as far down as needed until I could understand the top post.