My personal journey:

• arch is annoying to maintain and whil it is mostly stable, you do get some breaking updates here and there. It’s not a bad choice, it just doesn’t makeuch sense for a headless server.
• Ubuntu server, just why? Works fine but why?
• a not headless fedora, worked fine but still annoyed me sometimes
• proxmox (debian based) works great, annoyed me to manage vm resources.
• headless debian. Just works, I rarely if ever encounter OS issues. The only downside is that not everything can be found in the debian repos, but there is almost always an option to add a repo for whatever you want.

My setup is mostly dockers so keep that in mind.