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I'd recommend at least 512MB if it fits the budget. I have a 256MB one, but it's a tad small at times (fortunately I typically use it for text documents and source code). For going between a Mac and Windows, he'll probably want to format it as FAT32... I don't know what filesystems Mac supports, but I'm sure FAT is in there; Windows pretty much has FAT and NTFS, though there are drivers for others out there (e.g. ext2). FAT is probably the quick and easy way out, and probably the better for it.
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