Deleting old photos makes iPhoto go wonky

When I try to delete a photo that I've had in iPhoto for many years, the program freezes a bit, leaving the thumbnail. When I then try to import a touched-up version (saved as a jpg), iPhoto freezes altogether. I must go to Force Quit.
The deleted version never appears in the trash, but if I click on the still-present thumbnail, no photo shows. These are photos that I put in the first version of iPhoto, and have simply upgraded my OS and iPhoto over the years.
I did try reinstalling the library from my backup, but when completed, the same thing happened a second time.
(Is this a new problem with iPhoto 09 and photoshopped jpegs?)
So, at present my iPhoto will not import any photos that I touch up in photoshop, nor will it correctly delete these photos. This is a NEW problem. I have imported and deleted touched-up jpegs for years.
Latest OS and latest iPhoto
Help.

Why are you importing photos touched up in Photoshop?
You can set Photoshop (or any image editor) as an external editor in iPhoto. (Preferences -> General -> Edit Photo: Choose from the Drop Down Menu.) This way, when you double click a pic to edit in iPhoto it will open automatically in Photoshop or your Image Editor, and when you save it it's sent back to iPhoto automatically. This is the only way that edits made in another application will be displayed in iPhoto.
Note that iPhoto sends a copy+ of the file to Photoshop, so when you save be sure to use the Save command, not Save As... If you use Save As then you're creating a new file and iPhoto has no way of knowing about this new file. iPhoto is preserving your original anyway.
Other than that it sounds very like you have a damaged database file:
Option 1
Back Up and try rebuild the library: hold down the command and option (or alt) keys while launching iPhoto. Use the resulting dialogue to rebuild. Choose to Rebuild iPhoto Library Database from automatic backup.
If that fails:
Option 2
Download iPhoto Library Manager and use its rebuild function. This will create a new library based on data in the albumdata.xml file. Not everything will be brought over - no slideshows, books or calendars, for instance - but it should get all your albums and keywords, faces and places back.
Because this process creates an entirely new library and leaves your old one untouched, it is non-destructive, and if you're not happy with the results you can simply return to your old one.
Regards
TD

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