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OSX does not support *doc files. It can open some but does not handle some of the formatting options of Word.
I have Open Office on the mac but it does not convert perfectly all the time.
Best bet is to have Cutepdf on the Windows machine and print the files in .pdf format.
I have a Windows laptop and an iMac and found that is the easiest way of doing it.
I have had no trouble viewing video's on my iMac that I had created on my Windows machine. As Peter suggested, use VLC
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