I looked at the Trimble website and it says that the Ranger 3 uses Windows Mobile 6.5 for the OS.
If that is true, I think you can use RAPI. I have an example:
http://www.topwizprogramming.com/freecode_rapi.html
When I wrote this I had a Compaq Pocket PC and was using PocketBuilder to create apps for it. There was a desktop app that copied files to the device when it was placed in the cradle.