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Definitely earlier. I used these in 2011 while employed by a major government contractor. We had a stupid in-house system for paperwork submission that only worked on IE6 running on Windows XP. For my team I made an VirtualBox image based on this that could run on our customer-issued MacBook devices. Anytime we needed to submit expenses, just load the WinXP virtual machine.

Yes. You also get Vagrant images for them [1] which are quite convenient to use.

1. https://app.vagrantup.com/gusztavvargadr/boxes/windows-11

I remember those. I was more of a noob back then so instead of all the fiddling I often just used Browsershots.

True, I used them for IE debugging.