Itunes Won't add certain fully Compatible Video Files from Another Library

I recently updated to Leopard 10.5.2 on all my Mac computers. Ever since doing so, trying to add certain ipod compatible files to my Windows machine is touch and go. I have been doing the same add a file network transfer every day without incident pulling from three different Mac Itunes libraries. Until I went from 10.5.1 to 10.5.2. I can see, click, and request the file, but some files transfer without delay, others never copy over. I can't figure out why. One day recurring files with similar names transfer, others don't. I thought it could be a file name issue or directory name length, but I couldn't detect a pattern. The only way to transfer the file is to copy and paste to my Windows desktop, then drag and drop to my Windows Itunes libarary. Everything works fine that way, but it takes extra steps. Anyone have any ideas. I have no trouble with both my Mac and windows machines seeing each other and trasnferring files using explorer and Finder.

When this happens on my Win XP home PC, the file & folder have been mysteriously set to read only.
But you said yours were coming from a Mac, right?
In Windows, right-click on the file > Get Properties. I uncheck the read only box. Sometimes I have to restart iTunes. Other times I've had to restart the whole PC because the lock won't go away until I do.
Older versions of Windows had a nifty way to get rid of file locks on-the-fly, but they removed it in WinXP.
It's not just iTunes, either. These random file locks/read only settings happen with other files. I started happening about 6-9 months ago after a Windows update.

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