Using ITunes & with a Creative Zen Vision M

Did your player ever work with your Mac? The system requirements from Creative's page on the Zen Vison don't mention any Mac compatibility:

Minimum System Requirements
Microsoft® Windows® XP (Service Pack 1 or higher) / XP 64-bit
Intel® Pentium® II 350MHz or AMD K6-2® 450MHz
64MB RAM (128MB RAM recommended)
USB 1.1 port (USB 2.0 recommended for faster transfer)
170MB free hard drive space

Your best bet would probably be to contact Creative's Customer Support and see what they say. Mac compatibility issues should be something they are familiar with. You could also post in their forum or have a look at their Knowledge Base articles: : Creative Support

The MacBook won't speak to the Zen.

It's not supposed to.
-> iTunes for Mac OS X: Compatible Players<.a?

The Creative Zen is not natively compatible with the Mac. Creative provides no Mac software for their players. But there is an open-source project that might work for you, though iTunes won't sync with the Zen automatically:

http://www.wentnet.com/projects/xnjb/

If that doesn't work, then your only recourse is to run Windows on your Mac by one of the various methods and sync to your Zen through Windows.

It doesn't tell me why the 2 pieces of hardware wont talk to each other.

Since it would be up to Creative to make it compatible with iTunes for the Mac, you can contact -> Creative Labs and ask them why they will no talk to each other.

You can drag songs directly from iTunes to the player mounted on the desktop.