I should have read this thread before commenting on "playful" in the other thread! I see now what you mean by "playful." I did miss the boat on that :^) .
It sounds like you know yourself pretty well. I would be bored with a 30-item wardrobe also. And 30 items does not mean the same thing when you have four seasons vs. when you have only, say, two.
As for your questions:
#1: I liked the pants. I was wondering (as were others) whether they were just not warm enough. They look like a pretty lightweight fabrication.
#2: I liked the turtleneck dress with the toppers, but I didn't care for it with the sweaters.
#3: I thought the blouse looked great in all the outfits, even the one where it peeked out quite a bit beneath the sweater, which surprised me. That type of layering seems to be on trend right now.
#4: These pix make me think that I need to up my accessories game! I have very few, but you are right that they can really change up a look. I was just reading in a book how accessories are the key to having a successful wardrobe if it's going to be on the small side (which mine is).
#5: I didn't see anything that great about the pants. They were just kind of there. Since you have an abundance of clothes, I would get rid of them.
#6: I loved all the incarnations of the layered dress here.
#7: You look way better than I do in this weather! You can hardly see me at all (just a bit of my face!), since I'm so bundled up!
I think that your outfits all match your style goals, though I do wonder a bit about the blush thrifted blouse in this respect. The blouse is quite complex, with lots going on--the intricate details, the silhouette, and even what appears to be a lustrous texture. But if you love the blouse, you want to trust your heart, no matter what your predetermined style moniker is. :^)