Hey Eric... here's another interesting note. The old site used a code of some sort to deal with apostrophes in uploaded filenames. The new site will not read any previous attachments that contained apostrophes... rather, it knows they are there... you just can't download them properly.
I'm sure Vbulletin can handle them being there... I've done it at JTT... So it must be a carryover from the coding from the old site. Anything that had one before will have to be re-uploaded to the system.
Just another quirk I noticed. Not like you don't have enough being thrown at you right now