After a lot of testing old snapshot kernels and bit of git bisect and compiling I figured out the support for this non-standard boot was removed sometime around kernel 5.6.0. As of right now I'm still stuck on 4.19.
So... if you're doing MBR boot still on modern GPT disks, be careful upgrading your linux (any flavor).
My understanding was that CentOS does not even support upgrades between major versions, is that not true?
FWIW: I successfully upgraded 3 machines of mine yesterday. 2 Hetzner Cloud VMs, 1 dedicated server at Hetzner. I've never had any major issues during Debian upgrades since I've been doing them ~10 years ago. One time I hit a kernel bug [1] with my configuration, but that would also have happened without the upgrade.
[1] https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=931574
Historically, the upgrade process with Debian has been rough. RH & derivates always seem more resilient to the upgrade blues, to me. It's gotten a lot better, though.
This advice applies to Windows, macOS and Linux.