David,
A few questions regarding your DDA issue:
1. Are you using the DDA.exe that shipped with ArcPad 10.0, found in the "ArcPad 10.0 StreetMap Data" folder?
2. Does your data reside in the "StreetMap_Premium_NA_v11.3_Mobile_for_ArcPad" folder?
3. When you start the DDA, are you only adding the streets.sdc layer, or have you tried many different layers?
4. What options are you using in the "Extraction options" screen?
5. If you're just adding individual layers to the DDA, try opening the _navi_na.navmap file and attempt to extract all of the data for a small location.
6. Are you running the DDA directly from the DVD or have you copied the contents of the DVD to your computer? I've seen an issue pop up a few times over the years (not working correctly when run from DVD/CD but runs appropriately from the desktop) but I recently worked with a customer who was able to complete the process for v10.0 directly from the DVD. If you're running it from the DVD, try copying the DDA.exe and data to your computer and run it from there.