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I've been dealing with MS-DOS/Windows and Macintosh in higher ed environment for close twenty years now. I had a four-year break from Wintel on my desk while I was in a function where I could let my awareness thereof lapse. A couple years ago, however, I moved into IT security and so have re-engaged with Windows.
While Windows has gotten a lot better through the years, the Mac remains the better choice -- all other things being equal -- for someone who doesn't want to invest huge amounts of time learning how to configure and maintain their system. Windows is still somewhat clunky and confusing compared with the Mac, especially in its tendency to make one go to a number of different locations for what would seem the same or related configuration items.
Note that the Mac's ease of operation does not means less sophistication or power. It simply has a cleaner design.
While there can endless discussion of whether a given operating system is more secure than another, it is more difficult to keep a Windows system secure. Due to its predominant marketshare, the ovewhelming majority of viruses, worms and so forth are targeted at this platform.
Windows XP -- in its default configuration choices, new security features, and some better internal coding -- does represent a huge step forward, but you still need to run anti-virus software, keep it updated, and deal with the occasional varmit that slips through before your a/v vendor delivers updated definitions. Then there's spyware (and adware), which largely targets Windows. Beyond this, however, today's attacks rely less and less on vectors that can be detected and cleaned by traditional a/v software, and malware is becoming sophisticated enough that the only effective remediation approach is to wipe the system (aka "nuke from orbit).
Classic Macintosh did have its fair share of viruses, but there have been no significant threats targeted at OS X. One should, nonetheless, run a/v software on a Mac, at least in the interest of good citizenship (lest you pass along to Windows users). This is does not mean the Mac is inherently secure. It just isn't anything like the target that Windows presents. Poorly configured Macs can be successfully attacked, and we see the occasional compromised system. Macintosh can be vulnerable to exploits against a broswer or Java or Apache or PHP or any of the standard *nix utilities.
Still, for all practical purposes, the Mac is a more secure environment, even if only as a matter of security through (relative) obscurity.
As to availability of application software, Windows will offer a broader choice in many or even most areas, so you want to make sure that what you want and need is available on Macintosh. In a pinch, you can run Windows apps under something like Virtual PC, but most people view this as tolerable only for occasion use. For software packages that are available on both platforms (and even for some that aren't), file interchange with Windows users works fine.
People on the Mac may find it a bit harder to get help from others around them, but they'll need it less often.
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