Oh oh oh! How can I tell you how awesome this is?!
1) Thank you for the Grey Lady! I was hoping I'd get something involving her. 2) Sir Cadogan! I am so happy to see his backstory - so happy to see how he wasn't always the sort of Don Quixote figure he is now. It's excellent and fascinating! 3) Tom Riddle is completely in character.
Just - oh, I enjoyed this so much. The fact that you brought Tom in is the cherry on top: he's one of my favorite characters to kick around. And the magic! - I haven't really thought much about portrait magic, or what it would be like to be in a portrait, but now I want to.