I've always been slow to update to a new OS, mainly because stuff inevitably becomes broken especially since I write my own programs. Moving my HA server from XP to Windows 7 was painful for my .NET apps, so migrating from 7 to 10 wasn't high on my priority list. I haven't written many things in .NET lately due to problems I encountered migrating 7 or various Windows updates. Instead, I've been writing a bunch of Python scripts and running them on Raspberry Pis.
I started upgrading my kids' laptops to Windows 10. This was easy. I make them use Linux and they barely use Windows so I did clean installs for them. However, for my servers, I wanted to just do an upgrade and pray everything works. I started with the media server. I cloned the boot drive to a new SSD, stashed the original & then installed Windows 10. Surprisingly, everything worked. The big project will be doing the same for the HA server, but I'm not ready for that yet. Maybe as we get closer to the end date for the free Windows 10 upgrade, I'll feel more urgency. Until then, I'm happily surprised by how smoothly the media server upgrade went.