I was also the family tech support, and every time I saw someone go Mac, I never heard from them again. The Windows folks, have me clean up their PC every year and are calling every few months with another infection, another driver problem, another hardware issue.
I’m now on my fourth iPhone, and got a Mac Mini a few years ago to hook up to the TV. Turns out I was intimidated for very little reason. I didn’t understand it all at once, but it was damned easy (in fact too easy – I kept expecting I’d have to do something fancy or painful to make it work the same way my PCs do).
I’ve grown to love my Apple stuff and grown to hate how much excess maintenance, worry and frustration I get from Windows PCs. Now I tell people that if they don’t want to worry for 5+ years and just have the sucker work and stay speedy, get an Apple product. If they want to mow the lawn, make the bed and change the oil every time they want to do something like browse the web or write a document, by all means get a Windows system and start saving for its replacement in a couple of years.
I still know more internals and tricks for working with my work PC, and I’ll never be a guru about my Apple products. And what I’ve learned is, I don’t need to be a guru to be happy and productive with them. It’s very freeing when you realise that the PC promise of ultimate flexibility really means constant maintenance and incompatibilities. You really do get what you pay for.