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I'd add one more point that Linux has at least in my experience become easier/faster to install and fully patch than Windows. I also haven't not been having the driver issues w/ it that it used to have. That doesn't mean it doesn't kick you in the nuts occasionally though. It's easy when it works, but when it doesn't it's a gold plated bitch.
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Seems like a bunch of posters are multi-OS, so maybe this is a reasonable tangent.
I've always thought the *ix OSes were easier to patch. And that's going back to the FTP download, compile, install cycle. Package managers with integrated service management now make it even easier. Probably some of my earliest hate for Microsoft (MS-DOS was okay) was Windows and the mindnumbing serialized-dependency patch architecture they thought made sense. Okay, there were those Oracle script-driven updates of the mid-90s, where they would churn forever and
then tell you you didn't have enough disk space, exiting without caching any of the answers you'd had to enter. Uh, check sooner in the process? Cache? Think?
That said, I have rarely felt more helpless than when I would sit at a SPARC workstation trying to make all the not-quite-standard-but-very-cool pieces of software play nicely. It seemed to always be tied to a hardware issue, never my forte. I'm better with conceptual abstractions than with physical
things, and have fond memories of IEEE 1003.1 -- a really sharp group of people -- but hardware issues make my brain hurt.