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Sorry, but untrusted hardware can always win. For a case study of how hard this is to get right, see Microsoft's Xbox 360 and note that it was still fully compromised at least once.
Earlier quoted context omitted.
Most of the jail broken cracks are trivial to detect client side. Otherwise... They aren't going to pay anyway, might as well make the experience better for payers and not block on validation( but still track invalid transactions). And besides, if they're willing to install a hackers DNS server and ssl cert, they won't have money for long.
I agree. The hackers will only be a small percentage of your user base (guessing <=5%), if you have a problem at all. This issue is more problematic if you track revenue metrics, and so JB users may inflate your numbers considerably, if you're not cognizant.
Not if you're making a game for teenage boys.