not sure what your troubles are but try this:
I posted this deep in another thread, but I figured it may help more people if it was in the troubleshooting forum. As a former serial Pre brickmaker, I think I've gotten a sure fire way to get the webOS Doctor working if it hadn't worked for you previously:
1. Pull the battery from your phone, then replace it. Do not turn it on.
2. While holding the Volume Up button, plug the phone into a wall charger. You should get a big USB symbol on the screen.
3. Reboot your PC. Do not connect the phone yet.
4. Run the webOS Doctor program. Click Ok/Next until you get to the part where it wants you to connect the phone.
5. Connect the phone. It may take a few minutes for the Next button to become active if it is the first time you are doing this as the drivers have to load.
6. It'll take about 20-30 minutes to complete.
It worked for one person, hopefully it will help others...