Jacob,
Now that I'm thinking about it, I do remember an issue I've seen from time to time with that GeoExplorer 2005 series device. A year or so ago I talked with someone that was having a similar gwes.exe / device.exe issue with their 2005 series using ArcPad 7.1.1. I was not able to reproduce the issue on my 2005 series device, until I updated to the latest firmware. After updating the device firmware, I started to receive those errors, but only when browsing for files through Add Data.
A bug was logged for 7.1.1 related to this issue. A few weeks back, I got wind of the same issue happening in ArcPad 10 on the GeoXH 2005 series. This may be random, but that issue may have been related to Trimble's TrimPix.
Are you:
1. Using TrimPix?
2. Browsing for files when the error occurs?
If you're not browsing for files, at what point are you receiving these errors?