Okay, guys...here's the deal. Apple walked me through this, and while I have no clue WHY it works, it did work.
First, they had me delete all of the Apple software. (Directions below)
Then, they had me reinstall iTunes from the website.
Then, I created a new folder for iPad photos. (I already had one set up, but this was a second one.)
Sync the iPad with the new iTunes.
Put 10 or so pictures from your big basket of photos into the new iPad Photos folder and sync iTunes/iPad with the NEW iPad Photos folder. When these have successfully transfered over, put 10 or so more into the NEW folder, sync, and so on, until they are all in there.
It did work...it was a pain, but it did.
Here are the directions for removing all Apple software: (Taken from the page the tech directed me to.)
**Note** I had to go into and manually remove dll files, and quit said programs through the Task Manager, as they were hidden and running in the background. Follow ALL directions perfectly, or you will run the risk of screwing up your system. It takes time...
Overview
In some rare instances, it may be necessary to remove all traces of iTunes, QuickTime, and related software components from your computer before reinstalling iTunes. For most technical issues though, reinstalling iTunes is an unnecessary and overused troubleshooting step. If you are directed to reinstall iTunes by AppleCare, a Knowledge Base article, or an alert dialog, you can do so by following the steps in this article.
Notes:
iTunes Store purchases or songs imported from CDs are saved in your My Music folder by default and are not deleted by removing iTunes. While it is highly unlikely that you will lose any contents of your iTunes Library when following these steps, it is always a good idea to ensure that your iTunes library is backed up. If you're unsure how to backup, see iTunes: Back up your iTunes library by copying to an external hard drive.
These steps may take a significant amount of time to complete, depending on your system.
Steps
1. Remove iTunes and related components from the Control Panel
Use the Control Panel to uninstall iTunes and related software components in the following order and then restart your computer:
1. iTunes
2. QuickTime
3. Apple Software Update
4. Apple Mobile Device Support
5. Bonjour
6. Apple Application Support (iTunes 9 or later)
Important: Uninstalling these components in a different order, or only uninstalling some of these components may have unintended affects.
If you need more detailed steps on removing these components, refer to the following steps:
2. Verify iTunes and related components are completely uninstalled
In most cases removing iTunes and its related components from the Control Panel will remove all supporting files belonging to those programs. In some rare cases those though, files may be left behind. After following the previous steps, you should confirm that the following files and folders have been removed. If any are left behind, remove them now:
C:\Program Files\Bonjour
C:\Program Files\Common Files\Apple\
C:\Program Files\iTunes\
C:\Program Files\iPod\ Note: Follow the additional steps at the end of this article if you receive the alert "Cannot delete iPodService.exe: It is being used by another person or program" when trying to delete this folder.
C:\Program Files\QuickTime\
C:\Windows\System32\QuickTime
C:\Windows\System32\QuickTimeVR
If you have a 64-bit version of Windows, you will need to confirm that the following folders have been removed as well:
C:\Program Files (x86)\Bonjour
C:\Program Files (x86)\Common Files\Apple\
C:\Program Files (x86)\iTunes\
C:\Program Files (x86)\iPod\ Note: Follow the additional steps at the end of this article if you receive the alert "Cannot delete iPodService.exe: It is being used by another person or program" when trying to delete this folder.
C:\Program Files (x86)\QuickTime\
C:\Windows\SysWOW64\QuickTime
C:\Windows\SysWOW64\QuickTimeVR