On the surface this seems like an easy question to answer, but perhaps not.
I started using a Mac back in April of 95. This was right about the time that Windows 95 was released and the computing experience changed for millions. Up to that point I had used mostly MS-DOS and Windows 3.1, neither of which I would call a memorable experience, but playing Solitaire and Castle Wolfenstein was still pretty nifty. The company I went to work for that year used Macs almost exclusively, with some Windows machines on the side for various task specific requirements.
Within 6 months of being there, I became the "Mac guy" who did all of the maintenance and upgrades (on the side, in addition to my job) to all of the machines in the office, both hardware and software, as we had no real IT dept. Everything had until then been maintained by the Division manager personally. I even had the power to decide what new machines would be purchased for what tasks, who needed new machines and so on. I even got to do the Windows 95 upgrades on the Windows 3.1 machines. What a joy that was. That was when I really decided that Macs were easier to deal with. Anyone who installed System 7.5.x, 7.6 or 8 AND Windows 95 will tell you how much easier the MacOS, even then, was to deal with.
I acted in this capacity until the company decided to move to PCs and then they actually had to hire IT folks full time to make them all work together on the LAN and install software and so on. It was during my role as the IT guy that I went and purchased my first Mac, sometime in late 95, maybe September or so. With that purchase I never looked back, even after the company went to Windows boxes.
At this point, having stuck with the platform during the low days of System 7 & 8, Apples seeming road to oblivion, the return of the Steve, the resurgence of the Mac, the iPod and the fact that Apple is once a again making good products that are actually attracting customers who may have never even thought of one 6 months before, I figure I might as well stay. The OS keeps getting better as does the hardware. Sure in many ways Windows is as easy to deal with as OSX is these days, or OSX is as difficult to deal with as Windows is, but either way I suspect I'll never really switch to anything else unless I am forced to. I've been through the ups and downs with the platform, I might as well see where it goes next.