I owned several Toshiba laptops in the early 00's...they were atrocious, cheaply made junk, but they offered what I needed for the money I was willing to spend. After growing tired of having to have them serviced (by Geek Squad no less, which was a headache in itself), I wanted something different. My sister had bought a Macbook in 2006, and was very happy with it, expressing how much she enjoyed using it and how she would never go back.
I went to the Apple store a few months afterwards to check out what they had. The stores at that point were very different than they are now...not as chaotic, a lot more one on one walk in service, and having owned an iPod for some time before that (that i bought online), I kind of had an idea that their products were on a different level (especially given the cost, which to me was pretty high back then).
I sat down with one of the employees in the Apple store and he walked me through EVERYTHING...but at that time, Macs were still limited on what they could replace when it came to a very deeply rooted Windows based world. I was worried there would be things that I would not be able to do...until the gentleman showed me the machine running both OSX and Windows XP...I was sold. This was my way out. The price was still high, but after understanding the service I would be provided with the product, and the fact that the OS instantly struck me as inviting and nice to use, I was hooked.
I can't really say that the iPod I had so many years before represented any real decision for me to "try" Apple...it was more of a lack of option when it came to high storage MP3 devices. I really liked it, but it never made me want to buy anything else Apple related.