I used Macs for years at school, got an iPhone on June 29th, 2007, and got my first Mac, a MBP, in March 2008.
Before that, I was quite the PC. At the start of middle school in 1996 I had a Packard Bell 75mhz pentium on Win 95. Then I got an old laptop in Highschool that was a 150mhz Pentium on Win2k. Then I built a 1.9ghz Pentium 4 desktop in late 2001, built an overclocked 4ghz Pentium 4 in I think early 2004, then bought a Dell Inspiron laptop with a 2ghz Pentium M in late 2005 right before I went back to college. For years I had problems with viruses and needing to replace faulty hardware or other problems with Windows that would corrupt my files. One time I even had some guys from the IT dept show up in my dorm to confiscate my infected laptop. I had the latest antivirus and firewall software. My roomate at the time had a 12" PowerBook G4. He never had any problems! I was so jealous! After using macs more and more in class, I realized they just click with me. They're also great for artists. So I saved up and bought my first Mac and haven't looked back since. I've had a couple minor problems over the years, like waking up from sleep mode, or when changing file names I couldn't use the F key for awhile, but other than that, I couldn't ever see going back to the way things were before. It's nice to not have to work on my computer every week, but rather work with it to do the things I love!
Now I've owned every iPhone. The iPhone helped pull me over to the Mac side. I love it, but feel like Apple has messed up some with the iPhone 4. As for my next Mac, Intel's roadmap shows quad-core mobile processors arriving around the beginning of next year. I'm going to upgrade during the summer 2011, so I can get a bonus iPod Touch for my wife, who is still using my aging iPhone 1 as an iPod Touch. They will probably have 3rd gen Touches for free. Good enough for full iOS4 features like multitasking.
Overall, while my experience with Apple, iPhones, MacBook Pros and all the accessories hasn't been perfect, it's a whole lot better than the way things were before.