joshuaesmith, here is what Apple says "If the iPod for Windows Installer gets stuck at the "Waiting for iPod" message, you will have to close that window and use the iPod Updater to restore your iPod.
Click the X button in the upper right corner of the window to close it.
Proceed with the rest of the installation.
You will see an error message with the number 1628, which indicates that the installation did not complete. Click OK.
Unless you have an iPod shuffle, you will need to restore your iPod using the iPod Updater before you can use it with Windows. The iPod shuffle does not need to be restored to work with Windows." and here is how to restore your iPod "How to restore iPod
Verify that you have an active Internet connection, because you may need to download new versions of the iTunes and iPod Software.
Download and install the latest version of iTunes if necessary.
Open iTunes. Connect your iPod to your computer using the USB or FireWire cable that came with your iPod.
After a few moments, your iPod will appear in the Source panel in iTunes.
Select your iPod in the Source panel. You will see information about your iPod appear in the Summary tab of the main iTunes window.
If you are using a Mac, you will be asked to enter an administrator’s name and password.
A progress bar will appear on the computer screen, indicating that stage one of the restore process has begun. When this stage is done, iTunes will present one of two messages with instructions specific to the iPod model you are restoring.
Disconnect iPod and connect it to iPod Power Adapter (typically applies to older iPod models).
Leave iPod connected to computer to complete restore (typically applies newer iPod models).
During stage two of the restore process, the iPod displays an Apple logo as well as a progress bar at the bottom of the display. It is critical that the iPod remain connected to the computer or iPod power adapter during this stage.
Note: The progress bar may be difficult to see, because the backlight on the iPod display may be off.
After stage two of the restore process is complete, the iTunes Setup Assistant window will appear. It will ask you to name your iPod and choose your syncing preferences, as it did when you connected your iPod for the first time." Once you have the firmware on your HDD you should have access to all the function like disk and diagnostic mode. Hope this helps, good luck.