I finally bit the bullet to level up from Windows 8.1 to 10, and did an in-place OS upgrade. So far not too bad.
For reference, I still was able to activate Windows 10 automatically for free in Oct 2020. Totally expected I was going to have to spring for a new key, but I guess the existing 8.1 license was still eligible for the upgrade. No indication that was going to be the case based on a lot of prior investigation.
I’m super pumped to have a start button again. Fuck the Metro launcher forever.
Unfortunately, like the title says, I’m locked out of my Virtualbox Ubuntu server. After the upgrade, I can’t decrypt my volume. I’ve tried several different passphrases, passphrase variants, keyboard layouts, and LUKS commands, but so far, no luk. I’m not going to delete it just yet, but don’t expect to decrypt it at this point. Fortunately, I don’t believe anything critical isn’t already backed up there except for my emacs config which I’m a little bummed to lose.
The main reason I finally upgraded was I wanted to switch to the Linux subsystem, WSL, for running Ubuntu. I was tired of running into obscure build issues with my Windows Babun Cygwin install and fighting the Pact package manager over dependencies.
There are a few windows 10 quirks so far (have a really weird issue with my display adapter showing 4 extra monitors), but overall, it’s definitely an improvement. Still have to disable the nefarious telemetry, but it looks like it’s a keeper. The ability to quickly launch config and control settings with the windows key is a massive improvement. Should have had that feature multiple OS’s ago.