You make some good points about Winks' regression into a more conservative player, too. The bits about him being a perfectionist in regards to his stats and the toll his injury problems may have had on him especially.
Again, I liken him back to Cleverley. He was someone who favoured a high pass completion stat (as seen by some interviews he gave as a United player when defending his style of play), and also seemed to lose something about him after an injury away to Bolton in 11/12, and some successive ones the same season that kept him out for most of said season.
Before the Kevin Davies tackle, he was a really progressive CM those first few games and, during his loans to the likes of Wigan and Watford, he was pretty much an attacking midfielder or winger rather than a CM, and seemed to contribute well to said teams attacks.
I liked Cleverley but Winks is obviously a more natural footballer and, in general, just better, but his issues in regards to becoming a conservative player really does remind me of Tom. I digress, though!