Sync Error iPhoto to iPhone 3G

Tried to sync some applications from iTunes to my wifes iPhone. However, obtained an error message in that the file could not be found. After trial and error, by disabling the sync with iPhoto it syncs ok. One thing I did notice is that there are two photos that are left on the roll, although I cant see the thumbnails or able to delete. If tried restoring the iPhone to original setting and restoring from back-up - but same result, fails to sync once photos selected. Ive seen threads to remove the iPhone cache, but for some reason the file from the Apple ink will not display. Again the 2 thumbnails appear in the roll, but cant be deleted. I can sync my iPhone with no problem, using the same photos from iPhoto.
One other point, how can one delete old posts?
Mac Pro Mac OS X (10.6.2)