You get 500MB for the first upload (even if it's just one pic), and then you get 500MB for every 500MB you upload, so to get the most you have to upload 5GB or 4.5GB.
iPhone should work when you plug it in; it shows up in Explorer as a device with pics on it.
Not sure about the uniqueness though, while I know they store hashes for files to detect duplicates (I've had files I've downloaded from the Internet which I put in my dropbox upload instantly, which means they already had it and just recognized that rather than re-upload it) I don't know if they'd store them for deleted images.
So that might work.. upload 500MB of pictures, delete them out of drop box, unplug phone, replug, upload again, etc...
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Uncertainty is an uncomfortable position.
But certainty is an absurd one.
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