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Re:.NET on Linux – bye, Windows 10 by acdha on Monday October 17, 2016 @12:58PM (#12726819)
> Trying to upgrade an operating system is almost always a good way to ensure you're going to have a bad time.

That's a really strong assertion to toss out without supporting evidence. I've had the opposite experience with Debian/Ubuntu (100s of systems, starting in the late 90s) and OS X (dozens of systems, starting with 10.0) — the process is almost always start the update, reboot, resume work with rare exceptions for something like previously-undetected filesystem corruption.

Even my experience on Windows has not supported that conclusion – you might always want to be ready to reimage the machine but it hasn't been rocky for at least a decade.

The difference might starting and staying clean: avoid OEM Windows installs, apply updates regularly rather than putting it off for years, don't install system-level hacks (Mac users were terrible for awhile about using “haxies” and then complaining about Apple when some random binary monkey-patching broke on the next major release), and be careful about installing software from irresponsible sources.

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