I went from XP to 7, about six years after support for XP ended.
To make it even more exciting, I was running 64 bit XP pro. It seems that no one wrote printer drivers for that O/S, and I couldn't convince the 32 bit fellers to work.
So, I emailed anything I needed to print to myself, and printed from another machine. (at work, as I don't use one at home enough to justify owning one.) I went to 7 shortly after Firefox ended support for their browser on XP...... 7 was good, but, I still liked XP better...... 
I played with RedHat linux, and a couple other (much) older distros when I worked for Borders. (books and music, a company that no longer exists.....) But, my purposes at that time were work related, not gaming. Still running windows on my gaming machines back then. Now, I am retired.... for the most part.... just work part-time at a local computer shop. I don't really need the money, but, I enjoy the work, it's a cool place to work, and I get along with all of my co-workers. (a rare occurrence..... generally, there has always been at least one that no matter what I did, we just could NOT get along..... I do not miss that.) Oddly enough, I consider it "fun"..... (is there something wrong with me??)((you can lie to me, please.
))
I have a laptop that I use to talk to various automotive computers.... Might try some flavor of linux on that. Provided my software will run on it.
(yeah, I did the auto tech thing for many years as well. I like computers better. Smaller, cleaner parts, that NEVER see a Michigan winter.
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