I upgraded my ThinkPad to Windows 10 yesterday. It was a pretty uneventful upgrade. All of my software seems to work, including some stuff that I thought might be dicey, like Norton, VirtualBox, and OpenVPN. (Well, technically, I installed an upgrade to VirtualBox right after the Windows 10 upgrade, so I’m sure that fixed up the network stuff and whatnot.)
I haven’t had a reason to play around at the command-line much yet, but I’m happy to see that they’ve made some (much overdue) improvements to it.
The ThinkPad upgrade was smooth enough that I now feel like it would be relatively safe to try the upgrade on my main desktop PC. I may do that next weekend, if I’ve got nothing else to do.