1950s Windward two star, I would say 21.5" P2P. 275 USD. No-brainer.
Honestly, Jake, that might just be the best-looking C2 I've seen out in the wild, both in terms of fit and in terms of how well it has broken-in and aged. That's even counting my own C2, which I consider to be absolutely fantastic. Well done, simply superb.
I have not experienced any shrinking or stretching overall. However, due to the use of wrong hangers some of my jackets are misformed a bit in the shoulders. The jacket stretched a bit around the curves of the hanger, which gave the leather bumps in that area. So I, for one, hope jacket...