I would go to Options>Advanced Settings>Extensions and make certain both JPEG and JPEG2000 are "checked". Also, when you stated you have the ArcPad setting at Swerer99, are you saying the datum is set to Swerer or your projection file? Is this setting you speak of in GPS Preferences>Datum?
One other item, how are you transferring your data from your PC to the unit? Are you checking-out data from ArcGIS Desktop 10 via ArcPad Data Manager?