My mom switched to Mac. Result: I only have to really do something semi-serious (i.e. more than 30 mins work) once every 2 years. My (mentally handicapped!) brother uses a Mac. Aside from an occasional correction of his mail settings via ARD Admin I'm hassle-free.
My brother and his g/f still use Windows. I just spent four f***ing days reinstalling Windows XP because Vista figured Autocad was either already installed, couldn't be installed, or shouldn't be installed. I told them it was the last time and I would only support them if they bought Macs. Microsoft is a group of clueless arrogant monopolists as far as I'm concerned. Apple is also arrogant but at least they make something decent. Vista scared me into fits and out of family tech support for life unless they pay me $ 75,- an hour. That got their attention, I can tell you. After some "but what will we do then?" comments of disbelief I explained my motivations to them and told them the truth: Windows is a bloated platform with no vision designed by a company that is run more by lawyers than by true genius and I've given up on them completely. Sorry if this is a bit rantish (I suppose it is a rant) but I really want to underline it for you in simple terms: M$ is your problem.
I think Apple has several ups over Windows:
- it's designed to be learned by playing with it
- it gets out of your way instead of in your face
- it has a much, much, much clearer structure; people can find the things / settings they need more easily, and with less actions. Try setting up a dual monitor and occasionally attaching e.g. a beamer. It only costs 1 or 2 clicks after the 5 whole clicks you need to configure it the first time around. Try doing that in Windows and you're at least 20 clicks farther, and of course something or other b0rks along the way every f***ing time
- supporting it remotely is pretty much hassle-free aside from opening a port here and there (or else you could use something like Teamviewer)
- if you ever DO need to reinstall, the migration assistant will keep your settings whole, and you can drag/drop the software from the old installation; it's MUCH easier than reinstalling everything from scratch.
If you're in doubt, download it and stuff it into a VM and play with it. See how long it takes you to get mail etc set up. Now don't get me wrong - no OS is perfect, and OSX has its idiosyncrasies like any other - but it has a lot less of them, and any issues are usually fairly well documented. Just stay away from newest releases until the 10.x.1 update is out, at the least, and you will do fine.