ITunes won't sync certain photos from same roll to iPhone.

Okay here is the deal. Sometimes after importing photos from the iphone's camera roll, iphoto crashes during the process of deleting the images off the iphone. It usually happens halfway through deleting, so there will be a few photos left on the camera roll that have already been imported. I then manually delete those images from the phone.
Whenever I program itunes to sync the last 6 months of photos from iphoto to my iphone, it ALWAYS leaves out the images that I had to delete manually from the phone. This is driving me crazy. It doesnt give any error messages, nothing. It's just seems like business as usual until I get on my phone, go to the photos and see that all the photos aforementioned simply didn't sync.
I go back to iphoto and make sure that the images are there, and they are. I've even gone so far as to take the photos that won't sync, place them in a whole new album and sync. That works. They go into that album and show up on the phone effortlessly. But I can't really do that because there are literally hundred to thousands of photos like that throughout the last 6 months in my iphoto. I don't know which are which.
I have tried deleting the ipod photo cash folder in iphoto, but that didn't work either. It simply resized the last 6 months all over again, synched to phone and STILL left out any photos that were imported into iphoto, but not deleted by due to a crash, and manually deleted from phone by myself.
If anyone could help me with this nightmarish problem, I would be VERY happy.
Thanks a lot, Luke.
Rest In Peace Mr. Jobs. Thank you for making the world a better place.

Apply the two fixes below in order as needed:
Fix #1
1 - launch iPhoto with the Command+Option keys held down and rebuild the library.
2 - run Option #4 to rebuild the database.
Fix #2
Using iPhoto Library Manager to Rebuild Your iPhoto Library
1 - download iPhoto Library Manager and launch.
2 - click on the Add Library button, navigate to your Home/Pictures folder and select your iPhoto Library folder.
3 - Now that the library is listed in the left hand pane of iPLM, click on your library and go to the File ➙ Rebuild Library menu option.
4 - In the next window name the new library and select the location you want it to be placed.
5 - Click on the Create button.
Note: This creates a new library based on the LIbraryData.xml file in the library and will recover Events, Albums, keywords, titles and comments. However, books, calendars, cards and slideshows will be lost. The original library will be left untouched for further attempts at fixing the problem or in case the rebuilt library is not satisfactory.

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