I'd say that happens with 90% of sailors, and pretty much anyone who comes from leaners to cats (at least for the first bit of time on the new platform). And if you're sailing close to another boat, it's very hard not to start pinching.

I used to crew on a guy's Tartan 31 who was a gnat's eyelash away from being in irons every upwind session. He'd always say "look at all that real estate" between us and the leeward boats, but they always managed to sail on past us and we'd be the last boat at A. He bought a 135% genoa thinking that would solve the problem. It didn't. If it wasn't so fun to lose races with him, I would have jumped ship years before I actually did.

You've got windward helm most likely, so any time you're not paying attention your boat is probably going to head up. And you said it yourself - when I get resettled. Head "out of the boat" is always faster.

Your jib telltales are the quickest way to find out if you're pinching or not without having to look away for long. I guess the benefit of a 2-up boat is that the driver can focus on stuff like that, while the stringer could make the proper sail adjustments for the course being steered.