What I'm waiting for is a way around installing Apps on the iPhone outside of the App store, in much the same way there is software that allows ring-tones to be installed on the iPhone outside of iTunes.

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I - sadly - don't think that will ever happen on a non-jailbroken iPhone…

What are the implications of Jailbreaking the iPhone these days ... ? I have so much trouble with mine as supported by Apple that I couldn't bear to deal with any more problems.

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In my experience (iPhone 3G, jailbroken from a recent Intel Mac this summer), it's VERY straightforward, using the "official" Dev-Team tools. So easy I was nearly frustrated…