Hello,
For the first issue, ArcPad can sometimes lose the listing of datums in the GPS Preferences dialog. When this occurs, arcpad is unable to reference the GPS data to the datasets due to the loss of the incoming datum and hence cannot transform it to the operating reference frame. A blank GPS datum field (GPS Preferences > Datum) is indicative that the prjdata.dll cannot be found.
ArcPad looks for the prjdata.dll in the System path (default is: \Program Files\ArcPad\System) on the mobile device.
Also, when you deployed ArcPad 10 to the mobile device from the Deployment Manager, did you check to have 'Install Datum Transform/s for Windows Mobile' installed?
For the second issue, in ArcPad > Advanced Settings > Extensions tab, ensure that the correct image format is checked on to allow ArcPad to "see" the raster in order to add it to the map.
I hope these few things help out.
If not, please respond and let me know.
Thank you.