Sounds like the issue may have been with the support person rather than OS X. I've seen a number of Windows people who just never manage to get past the fact that OS X simply doesn't behave like Windows.
I'll chime in with my own experience. I bought a PowerBook expecting it to "just work." I've used DOS, C64, Various Windows, currently Linux, and way back when, even punch cards. Yes, I'm flexible and adaptable.
I really wanted to love the Mac, but at the end of the day, after three frustrating years, it just never did things the way that I wanted it too. Not big stuff, just lots of little things that drove me away.
There were lots of things that didn't "just work," or only worked with one official Apple sanctioned product, or required you to work in one specific Apple designated fashion. And there were a handful of things that, after three years, I never managed to make work well.
The problem is never that Windows (or Linux, or whatever) users "can't" understand how to use Apple products. The problem is that Apple insists that you take their whole world view, hook line and sinker, to the exclusion of all other ways of working. There is the Apple way, and it is the One Way, and the Only way.
Some people find that works. Some people are happy to take whatever comes preinstalled and live with it, apparently not caring that there are other, sometimes better ways to do things, more powerful applications, and even more intuitive ways to design some UI elements. Some people are happy to buy Apple hardware to attach to their Apple computer to run their Apple software, and don't feel the need to look at anything else. Likewise, some people are happy to live their whole life with twenty-five albums on their iPod, that they previously owned as CDs, and before that as LPs.
Finally, the real differences between a Windows Desktop (pre Windows 8 anyhow), an OS X desktop, and Gnome or KDE desktop are really just cosmetic. The desktop paradigm (icons, menus, some kind of task bar, drag and drop) is pretty much universal, and no-one really has an issue moving between platforms any more.