We like the ‘Easy’ button, and most people do. In fact, Apple’s products have always been marketed that way, and they usually are . . . except when you try to switch platforms with one.
There is easy-to-use Mac freeware for transferring files to non-Mac devices/computers, to avoid issues. Kopymac–available online. And here’s a thread on Mac issues.
I read in multiple forums about people having issues when connecting non-iPods to Macs, often enough that I cannot in good conscience recommend the practice to others…especially if they have ready access to a Windows machine, like the OP.