It's quite possible that security patches can only go so far before there is more patch than program, and there comes a time when ever advancing hardware means that a time comes when a ground-up restart is the best answer. Whether that results in a better system is a bit hit and miss.
To that end, I got on well enough with Windows 3.1, didn't really see the point of W95, but got on OK with it. Liked W98SP2, avoided ME and W2000, Really liked XP, couldn't see the point of Vista, though W7 was great, detested W8 (not on my own, there) and now that W10 looks and feels like XP / W7, I find it acceptable. Apart from one or two areas where some lumpwit in Seattle thinks that he knows best. I don't know how available personal entertainment drugs are there, but I have suspicions.
Any new toys that I buy for use on W10 are likely to work because they have current drivers. The same is not true for older versions.