I'm a seasoned professional Linux sysadmin, so getting a distro installed has never been a problem for me (thanks to my first proper distro being Gentoo).
In the end, it's the stability and "knowing what to expect", that always makes me come back to Debian.
ChojinDSL
It depends on your use case. In my case I mostly manage bare metal servers running certain services or docker.
For servers I don't want rolling releases. That just means stuff is going to break on a regular basis. In my opinion, Arch Linux is the worst offender here. I don't know if it's gotten better since last I used it. But with Arch Linux the problem was, that you had to keep up with the updates. If you forgot to update some machine in a while, it could happen that you missed some update that changed some critical things, and everything else already moved on, and the only way to fix it was to hunt down the intermediate package version and try to install that manually, or just wipe and reinstall.
As far as "ancient" tools is concerned, it depends on what those tools are. Bugfix and security patches is what I'm most interested in on a server. Just because there is a newer version of software out there with some new features, doesn't mean that I need those features, or that they're relevant.
For the cases where I need something newer, there's docker, flatpak and backports repos, (if not third party repos for certain tools).