Funny; Vista was the reason I switched to Linux as well.
dos was the reason i switched to linux. (sorry, i could not resist, i am old ;-)
7 was fine, but in retrospect it was a bit of a dead cat bounce.
I have one Linux -> Windows migration story that went really well. Early-2000s, I worked for a company that printed massive amounts of data and shipped it to clients. The data had to be printed and shipped, digital delivery wasn't an option at the time (legal BS). The Unix/Linux sysadmins were using a Linux box as a print server, having trouble getting a newly purchased, super expensive printer to print correctly. They worked on this "project" for weeks. The printer manufacturer didn't have a Linux driver and wasn't going to make one, so the internal team was trying to write their own. Finally, I told them to just use Windows as the print server; the Windows drivers are right there on the company website. The idea received relentless pushback: Windows can't handle the load. Our automation uses Unix-only protocols (ftp) to copy the data to the print server. Windows is too expensive. Finally, I took an old desktop PC, installed Windows 2000, added all the required printers, including the new, expensive printer. Installed all the manufacturers' drivers. Then I installed ftp, added the matching auth credentials, and it was done. The whole process took me, maybe, 2 hours. Naturally the sysadmins that owned this process were pissed; they hated it. But their boss loved it and it became the solution. Linux -> Windows FTW.
Microsoft's recent track record with Windows 11 seems to have kickstarted another Win -> Linux migration wave.