I'm pretty sure I already have the answer to my question but I need it confirmed. Is it possible to configure ThinOS devices from WDM Workgroup edition? I can make new configuration files and I can deploy the package but it always fails. From what I've read it's almost as if I would need to use Default Device Configuration, which isn't available in the workgroup edition.
That is correct. To do what you want to do requires WDM Enterprise, however, you can manage your WTOS-based thin clients using an FTP, HTTP or HTTPS server. For more details, see the WTOS Admin Guide available at www.wyse.com/kb
That is incorrect, you can certainly manage WTOS devices from WDM workgroup edition. I can easily set up group profiles and do things like pre-configure RDP connections and associated settings, manage monitor settings, and do firmware updates. The documentation is horrible, but once you figure it out, it can be done.