The height of the front of the cage against the large ring is maybe 1mm. It doesn't touch but just barely. The back of the cage is raised though. I'll try to get this aligned.

The frame is a 2006 Kuota Kredo, not a common one. If anything the seat tube is more upright.

The big/big combo is what the video says to try, not to use it but for testing the shifting as that's the extreme. I've had an instance where I was going up a hill in the big/big and then shifted and the chain dropped. Since I was going uphill, I lost all momentum and couldn't unclip and joined club tombay. This is the situation I'm trying to fix. It isn't good practice I know to be in big/big, but when you are and you shift it should still work. Everything else works. At least here in NYC I'm almost never on the small ring anyway. There aren't all that many hills here to climb and mostly I stay on the big ring on the few that I do.

Chainrings are actually recent and not worn, but aren't brand new either.

After I posted I tried multiple times and it worked with the bike on the trainer, but that doesn't mean it'll work on the road. I think I'll try to make the curve match the chainring better.