I went from XP to 10. I lost most of my fav plugin/VSTs in the process but that's fine as I'm keen to limit myself to the ones that I use often & well.
I had to upgrade when the interface with the XP started to have problems. New interfaces weren't XP compatible so I took the leap.
W10 is great with BIAB & Reaper so I'm pretty happy.
I've kept the XP machine & all associated gear and boot it up from time to time to ensure it's working. I made copies of all its contents to a couple of SSD/Ext HDDs so I have the machine & a back up.
I'm down to about five VST/Plugs I use regularly with about 20 for occasional/specific purpose use.
Now W11 worries me - hope fully the stupidity and fallout of the subscription stuff & needing to log on "online" has been resolved by the time I need to do it.

Cheers
rayc
"What's so funny about peace, love & understanding?" - N.Lowe