Thanks for the clarifications Steve.
Maybe the work is not as much as Undertow at the time, that's true. But my gut feeling says getting to 100% compliance can be rather time consuming nevertheless. I've done a number of patches for our company on the GF codebase (similar to Payara still), and I remember that the Tomcat parts are quite entangled with GF. That's probably where you would spent most of your time quota.
I saw the DI TCK patch for HK2, it's quite minimal, just a technicality really as HK2 was already supposed to be DI compatible. If you haven't started yet with the actual CDI work, I stand by my earlier statement it seems like very little time to me.
Yes, it depends on the Jakarta EE 10 timeline. Many specs have set their deadline at mid October, meaning a final release in November or December? The joy of roadmap planning, I know all about it (I do this for my company). With holidays in between and some staffing issue I read about at Payara, 4 to 5 months would be a miracle if you could pull that off. Wish you good luck :)