Found upgrades mildly annoying with GitLab, big reason I moved to Forgejo for my personal stuff. Far easier to setup and maintain for me, seems to be happy with caddy and runners are really easy to setup.
I’m not hosting for an entire org though, it’s just me and I keep all my selfhost stuff local only, so obviously YMMV.
Powershell, windows terminal and winget are all legitimately nice tools, powershell especially is just stupidly more powerful than it needs to be (and verb-noun syntax is great).