HeresMyAccount: And digitally, no less
edit: What gives you that idea? If you can connect speakers, it's analog. And I still have to see a digital microphone port.
No, what you get is digital -> equilizer -> analog -(cable)-> sampler -> wave file.
The result may or may not sound good, but it will not be the original. It might still suit your neads, but if it' about music and you want to stay as close to the original as possible, re-recording it is not the way.
It depends on quite a few factors, the D/A transformators in the iPhone and the A/D sampler used in the sound card.
The iPhones audio connector is meant for small headphones, not for speaker amplifiers and definitly not to be connected to somethings microphone port. I ignore digital equilizers for the moment. Small earpieces usually have very bad bass, so the port is calibrated to counter that. On speakers or your PC the bass might be much too loud.
The sample rate might make a difference I don't know what the sample rate of the iphone output is. If you take a 16 bit file, reduce the volume by 15% on a 16 bit sound card, you get rounding errors. Therefore most modern sound cards work with 24 or 32 bit, so you can reduce volume and are still pretty close to the original. Older 16 bit cards try to compensate the errors through their capacitors which flatten the output a bit.
The small chips in an iPhone can't compete with the capacitors on more expensive soundcards anyway. People who use their computer to listen to music don't use onboard sound or USB headsets, but soundcards like certain Creative Soundblaster or Asus Phoebus models. But not even these produce a 100% accurate sounds, they also are designed for certain speaker settings and calibrated that way. Also they usually have separated headphone and speaker ports with different setups.
The microphone port is meant for microphones of course, enhancing speech frequencies and reducing noise on other frequencies to get the most clear speech. Also the impedance of microphone port is not what a audio port for headphones would expect.
If you have one, use the Line-In port instead of the microphone port, Line-In is meant to stay as close as possible to what comes in, this way the only 'error' source comes from the iPhone.
So in short, I can only repeat what I said at the beginning. The result might still be what you wanted to get, but it will not be like the original.
If you really want to get the same file, you need to transfer that file and it may prove a lot simpler than doing a re-recording, cutting it and so on. Why not give one of the named file transfer programs a try? It might prove a lot simpler than you thought it is.