Status update:

HolyForest, thank you for the Onyx idea and the disk memory suggestion. Both carried out.

thomllama, permissions repaired, and still no go. So I'll be messing with images next...

Thank you both for your ideas. I am still hoping to get this to work.

If images are indeed the culprit, is there any good work-flow algorithm to minimize the hustle of transferring the files from Windows to Mac?