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I see a free data hack: Load a version of iMessage that never acknowledges the message, but saves the data (and doesn't brick the phone). Send lots of data, acknowledge via other means (checksum sent over email etc). How much data could be sent this way? GBs?

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This doesn't work with iMessage, because the carrier sees iMessage no differently from any other kind of data download. However, a friend of mine tried doing something similar using the <number>@txt.att.net (or equivalent for your carrier) email-to-SMS trick and wrote an Android app that parsed the messages. They promptly received a firmly worded email from AT&T and were forced to abandon the project.

I'd definitely like to know more about the project.

Why did your friend choose to send data over SMS? Why was AT&T upset at his project?

It doesn’t work that way. The person with a cell bill will still be charged the downloaded data.

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