Windows

You're not going to get more hand holding than you'll get with Windows.  This is regardless of whether you talk about Windows 11 or Windows Server.

Know that Windows Server comes with limitations that the desktop version doesn't, even though it has a desktop environment that is pretty much the same.  So, don't expect to have a fun time running Crysis or whatever on it.

Expect it to have significant performance hits compared to Linux.  Expect to have to either pay extra or put in extra effort getting some things to work with it.

You can run containerized apps through Docker on it and do most other Linux tasks on it.

Honestly, if you're already neck deep in the Windows ecosystem and just want your hand held to the maximum extent, it's probably the best choice.  Don't expect to have a fun time running VMs or scaling stuff.

I really don't recommend using Windows as a server OS.  There's a reason Linux absolutely dominates that market.  I can't overstate the inconvenience and performance hit you'll take running this over literally any flavor of Linux.

However, it's worth noting that there are certain circumstances where you might want to pick Windows due to certain hardware or software.  Now, most of that hardware and software isn't going to matter much in a self hosting environment but maybe you have really specific needs.