Awesome picture!
I think what happens is that I sail crappy and/or make tactical mistakes when I first go out, but I make it work to some extent through sheer power. Then my energy gets drained out, the reality kicks in and my mistakes are severely punished. After receiving a good amount of beating I wise up apparently at some point and start sailing smarter and have my great finale . Like for example yesterday after Chris left I started jibing at the far end where it was flat and tacking at the launch side where the chop was bad. This helped me to have more successful turns and to stay upwind at the same time. It takes too long unfortunately for my brain to process the information.
Ha, i do this almost every time on my 94, regardless if I want it or not. Im not going to do a planing exit with it any time soon. It's just that you have more speed and you can point higher then me. Skill, weight, equipment-everything contributes more or less. The reality for me is that if I don't tack a walk of shame may follow...or a long upwind shlog at least.
PS: actually crashing may be the main reason for my difficulty to stay upwind. And I crash a LOT, as you've seen. Every crash results in downwind driftting and then I have to bear off to get planing and there you go.