Some time in the early 90's, my dad dumped his KayPro for a custom-built, unbranded, 386-based PC running Windows 3.11, which I inherited from him after he upgraded yet again. It was the first computer I had all to myself. After learning my way around the Mac's interface, learning Windows 3.11 took all of five minutes. The PC also had color graphics, which was a definite improvement over the black-and-white Mac Classics at school. I didn't get much actual work done on the PC, though, because nothing I produced on it was compatible with my high school's Macs; I mostly used the PC for games.
My high school actually had two computer labs: one full of state-of-the-art Macs for basic computer training and programming, and one full of ancient, DOS-running IBM PCs used for business-related classes. I spent ninth and tenth grade learning how to program in HyperCard, which I used to create a couple of graphic adventure games complete with an X-Y navigation system that took quite a while to code properly. One program I developed in tenth grade on the Mac LC III was an Aliens vs. Predator adventure game, with graphics taken straight from the Dark Horse comic series and audio from both the Aliens and Predator films. I also created a HyperCard-based trojan to mess with the other kids in the lab. It was basically just a HyperCard stack that, once launched, would auto-generate new cards until the RAM filled up and the Mac crashed. High school was a high point in my experiences with Macs, but for the rest of the 90s and the first few years of the 2000s, it was all downhill.
Once I got out of high school, my long relationship with the Mac went on an extended hiatus. After joining the Navy in 1995 I hardly used computers of any kind for several years, to say nothing of Macs or the Internet. For almost four years I barely touched a PC for anything other than playing video games. Macs didn't register on my radar at all, and the few times I came across one, I had the same reaction that a lot of today's Mac haters still have: "For as much as they're charging, I can't even get any decent games for this thing?"
In late 1999 I finally started using the internet on a regular basis via a 56k dialup connection through my roommate's ancient and thoroughly crappy Performa. I don't know which model Performa it was or even what OS it was using -- it was either OS 8 or System 7 -- but I was not impressed with that machine at all. When my roommate offered to give me that Mac in exchange for me paying his part of the rent for a couple months, I turned him down, because I hated almost everything about that Performa. When I moved in with my girlfriend of the time, she had two computers: some anonymous box from HP running Windows 98, and an iMac with OS 9. Since the iMac didn't have any games for it, wasn't compatible with our cable modem, and had that horrible piece of garbage hockey puck mouse, I wouldn't go near the thing. I preferentially veered toward the HP machine for everything I did.
From mid-2000 to early 2003 I once again barely even saw or used a Mac except for the handful of times I visited a Mac zealot friend of mine who lived in Seattle. I inherited yet another ancient computer from another friend of mine for my home use, one even older and less capable than the Performa: some Gateway box running Windows 95. Unable to even hook that machine up to the internet or run 3D games of any kind, the Gateway saw little use for the two years I had it.
After almost ten years of using computers solely for internet access and the occasional bit of gaming, I'd become sort of a luddite. Beyond basic word processing and web browsing, I really had no clue how to use a computer anymore. I ended up becoming a Mac switcher in early 2003, completely against my will, when I moved in with my wife. She had a dual 1GHz G4 Power Mac running OS X, and for the first couple of months using it, I had no idea what I was doing. I think my ignorance showed through enough that my wife got paranoid of letting me use her Mac at all. I eventually got the hang of it, but it was a painful process; I insisted on using Internet Explorer, stayed well clear of OS updates, and didn't even attempt to do anything out of the ordinary with her Mac.
It was only after buying a used PowerBook G3 off of eBay for $200 that I really started figuring the Mac out. In the process of upgrading the processor to a G4, upping the RAM, swapping out the hard drive, and hacking the thing to run OS X Panther and Tiger (the model of PowerBook I bought was supposed to max out at Jaguar), I quickly gained an appreciation for the ins and outs of OS X. In the process, I reached the point where I flat-out refused to use Windows unless I absolutely had to for some reason. Within the space of a year, I also went from being completely ignorant about computers to being free tech support for all my friends; and for the few of them still using Windows, my first bit of tech advice is almost always to stop using Windows. OS X may or may not be inherently "better" than Windows, but over the past several years I've figured out that I only get the urge to throw my Mac out the window once or twice a month versus once every five minutes with the average Windows box.
My wife upgraded to a MacBook in 2007, so I inherited her Power Mac -- just in time, as it turned out, because even after all its upgrades, my PowerBook was definitely showing its age, particularly in the way it liked to chew through hard drives. In February of 2008 I bought the 17" MacBook Pro I'm still using today -- the first brand-new computer I've ever owned.
It's been a long, weird ride -- BASIC programming, typing tutors, HyperCard programming, then close to ten years of neo-Ludditism -- to where I am now, in a house full of Apple-branded gadgets, most of which would have sounded like science fiction when I sat down in front of a Mac Classic for the first time twenty years ago.