There was a time when browsers limited file names to 32 characters - and PhotoToWeb tried to honor this by taking a subset of the name to use. I wonder if P2W was reducing I.FEST_04-22-06_JPG_Daio Hofmann_ 94.JPG to somewhere BEFORE the _94, and so each photo would be getting the same output name. Try this:
1. In a terminal, copy/paste this next line:
default write com.stone.PhotoToWeb LongNames YES
2. Relaunch PhotoToWeb, and output the pages - did it work?
Let me know!
This hidden default will allow long HTML and IMAGE names (up to 64 characters total) Note - old mac os 8 web servers have a 31 character limit which is why this is off by default.