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I haven't owned an iPhone in over 5 years, and I feel the same way. No company should be romanticized, and I'm sure Apple's (very public) decision to take user privacy seriously can be viewed cynically - but at the end of the day that's the kind of stuff I care about as a consumer, and will choose my next phone accordingly.

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As an N.B. - developing and using for iPhone/iPad, hell even Apple TV has become so much nicer in the past 5 years. I can't remember the last time I've used DFU mode. Signing Certs are still annoying in XCode, but day-to-day it's a lot better than what it once was.

Do you still need an up to date mac to do it (even a hackentosh) or can you develop from outside their environment?

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