Christmas 2002 - "iceBook" iBook G3 700 with 10.2
I guess I have switched a few times -- Vic20 to C64 to Amiga to Windows 95 to NT to OS X. My favourites (for work AND play) are the Amiga, and now the Mac.
I switched to the Mac when I felt that the entry-level machine (at that time the 700/CD iBook) had enough horsepower to handle digital video editing. My Amigas were the king of multimedia, but just as digital video editing cards were coming in, I switched to PC because it was a little cheaper. (In retrospect, I would have saved MANY hours, many dollars and many headaches by buying an Amiga 4000 with Video Toaster Flyer for editing, instead of building a powerhouse PC that was never 100% reliable.)
A few short years later, and the consumer laptop from Apple could kick the butt of my $10,000 editing PC. I ordered an iBook, maxed the RAM, and put a couple of LaCie firewire drives on it, and never looked back. That iBook edited my first feature film.
My iBook is still going strong. It's running 10.2.8, though I'm getting tempted to update the OS.
I have had the dreaded iceBook logic board failure, but rather than put me off of Apples, it has made me a dedicated customer. At about 4 years old, my iBook was long past warranty, long past the extended warranty for logic board replacement, and didn't have a matchine serial number for extended support anyway. And yet, the local Apple store politely and professionally took my iBook and replaced the logic board, completely gratis -- saving me nearly a $1000 repair. I upgraded the hard drive, and had an essentially brand new laptop. It still churns away every day -- my wife prefers to use the iBook because its small, convenient and speedy for all of her needs.
I was so impressed by Apple's service, I didn't hesitate to snap up an iMac G5 - now the main machine in our house.