I just think he's a bit rich walking into two PL jobs. Look at someone like Hasselbaink who started at a small Dutch club and is now at Burton. Or McClaren who was more than willing to go back into the Championship and abroad after being the England manager.
Sherwood's lack of enthusiasm for the myriad of coaching jobs that have opened up besides PL ones is a big question mark: he hasn't proved himself anywhere, and he isn't willing to.
I don't think that's fair; he was given the position at Spurs on a temporary basis after AVB went, and a string of good results got them to extend his stay until the end of the season. He hardly walked into the position, he had a good record as their youth coach and then proved himself capable in the short term.
Obviously he ended up looking a bit of a wally but I think he was justified in feeling his results in the half season with Spurs were enough to get him another chance at a Prem level club, or at least promotion contenders in the Championship.
I don't expect him to do well with Villa myself, though I do think they will stay up (which I suppose some might say is doing well)