Long post incoming
From the age of about 9 or 10, I was very much a PC person. Had my own Sinclair 8086 based machine and was obsessed with the single 286 class machine we had in school. Over the years I bought and upgraded through 286, 486SX, 486DX, Pentiums, K6s, AMDs... the lot! . Due to being a nerd, I was pretty hands on with my gear and the side panels were permenently off and hard disks hanging on for their dear life. I blew up a lot of gear.
During the entire time, I was staunchly anti-Apple. Anyone who knew me knew, even before my teenage years, I hated those machines. I didn't have a console so wasn't part of the Megadrive vs SNES wars, but I had my own. And goddamnit, I was sticking with my side.
In around 99/00 I was doing work experience at a local magazine and one of the designers was showing me proudly around his iMac. It was presumably running OS9 at the time, and it didn't little to sway me. I went downstairs and used some horrible aging machine to write my articles on because 'I was a PC guy'. I'd rather suffer on antiquated hardware than put up with one of those...things.
Fast forward to 2007, and my mother suggested purchasing a laptop to see if my dad could use it. He'd recently become very badly disabled, and motor skills were very poor. While I'd never buy a MacBook myself, the keyboard layout made me think it might be something he could adapt to with help and I was friends with a Mac advocate who I'd spent many hours argueing with, and thus had a bit more hands on with the machines. I picked up a machine from my old university that was brand new and at £200 less than retail via eBay.
Unfortunately, while my father was able to send email with a huge amount of assistance, it wasn't viable to use when I wasn't visiting and the machine was kept in their cupboard for most of the time. One weekend I stupidly forgot my laptop, and grumpily grabbed the machine and made a user profile just so I could go online. Over the next twelve hours I customised the OS behaviour to my liking and downloaded the equivalent apps to what I was used to running on my Packard Bell XP machine (wasn't bought out of choice, it was from a trade and I'd promised myself a better laptop in the future). I was completely won over.
Since then, I've owned a CoreDuo BlackBook, a Core2Duo MacBook, a late 2007 MacBook Pro, an iPhone 3G and 3Gs, a 2010 i7 Quad 27" iMac and two days ago I purchased my mother an iPad for use in bed after she recovers from an operation shortly. Every time I read Windows users defend their platform with vigour, it reminds me of how I used to see computing. I was the kind of person who wanted to use a machine for the sake of using it, now I simply don't want to deal with the hassle of sorting out the problems that come with it. There's something so wholey different about the way Apple approach their systems that no other company seems to be able to get. Who else can make a product (iPad) that my friends 90 year old 'never owned a computer in her life' can get excited about as much as I am?
People can talk about the 'reality distortion field' or 'idiot fanboys buying anything with an Apple logo on it', but it's more than that. Walking into an Apple retail store is so much different to walking into PC World. I've had problems because of the amount of gear I have, and the torture I put it through. The turnaround on fixing or replacing my damaged goods has been amazing each time. Now I can ignore specifications, and simply ask myself 'does this do what I need it to?' and I've never had a problem since then.
Also, anytime someone asks me to come spend hours fixing their horribly, horribly broken PC I can simply respond with "Sorry, I only know Macs". If that's not a reason to switch, I don't know what is!