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Roxio MyDVD 8 does not have that limitation.

Include up to 999 photos in each slideshow DVD menu

Now that said, it's not quite the same as a browseable disk, but will auto play them.
 
http://www.roxio.com/enu/products/mydvd/premier/features.html


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Windows itself has a max of just 260 characters

Well that is a bit ambiguous.  Windows 1,2,3.1,95,98,ME,2K,XP,2003,Vista ?  FAT12,FAT16,FAT32,NTFS ?

Which one are you speaking of generically there?

NTFS supports up to 32,767 bytes for a path, with a limit of 255 Characters per each filename\foldername in the path till you reach 32,767 bytes.

Now if you're talking FAT12 / FAT16 then yes the OLD outdated DOS does have that limitation.  I would guess that all Windows versions running on FAT16 would also have that limitation.  Those on NTFS though do not.

The FAT32 does not appear to have a defined limit though one should not try to test this limit as you will find other software and drivers (even those included with the OS) will not support extremely long paths.
 

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