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4. Do they work for dry eyes when sleeping under a fan?
Yes, I gave them to a friend who has major eye issues. She loved them. They don't sit right on your eyes. There is a space there and it makes it very pleasant.
 
5. Can this be machine washing?
Yes, but we suggest you put it in a laundry bag to help it last longer.
 
6. If you lay on your belly (so mask partially mashed into pillow), will the mask press against your eyes?
Not really... Only if you're face down on the pillow and then you wouldn't be able to breathe so it wouldn't matter. :-)