I don't think Windows is a good comparison, since major upgrades for it tend to be vastly more invasive than major upgrading the average Linux distribution. Debian 6→7, ten years ago, was a really massive infrastructure upgrade, but ever since it's been pretty smooth sailing. Ubuntu is a bit bumpier, but it's still only on the level of Windows' "major feature upgrades (that totally aren't service packs because we don't want to extend your warranty)" updates that Windows 10 and newer get every 6 months.
And Windows 7 is extremely old and only works with new software because, and as long as, developers go the extra mile to make their software work with its old APIs. Valve recently announced that they'll drop support for it next year, and other companies will follow soon. It's not too much different from the situation of, say, Debian Oldstable or Ubuntu LTS: Outdated, but popular enough that people tend to put in the effort anyway.