I have the same experience with home/family support. I work in IT at a college and I can also explain computers and their functions to people so they understand and replicate what they need.
I bought my wife and will be giving my children Apple machines. Easy to use, has a pretty decent command prompt, is transparent as I want in most circumstances, rarely needs a restart, and well, is just the best computer for the money. I don't see it as that "Luxury." Buy a used/refurbished iBook/MacBook or iMac or MacMini and try it out. Get the warranty. Use an educational discount. Show your cleavage and ask for discounts. Save your coffee/beer/weed/crack money for a couple of months. Whatever. It's still worth it IMO.
I would love to switch my extended family over to OS X or Linux, but they choose to stay with Windows. God anything would be better than windows. Fucking Minix would be better than Windows.
BUT
My father-in-law "has to use Outlook." That's just a shitty policy for any company, yes, including blue shops, but let's not get into that. That ties him to Windows. Period. No Parallels, No VMWare, and hell no WINE.
Same with all my other extended family. They have some app they cling to or "don't want to learn a new OS." Most don't even know what an OS is. How do you overcome that? Put it on things they use. If you have some amazing netbook that everyone wants, they will use Linux if that's what comes on it. If some amazing phone comes out that natively runs linux and gets market share, then people will use linux.
I'm just happy that Dell and ASUS offer Linux support at all.