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1.) Are the earphone outs (on the 40GB model) proprietary to the apple earbuds or are they the normal mini plug connection?
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Normal 1/8" plug
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2.) What are your thoughts about using a headphone jack as opposed to a normal level line out? I am afraid of having to constantly worry about volume levels.
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It's always best to use the line out rather than the headphone out...well that's what most people prefer (myself included) simply because the signal is much cleaner than through the headphones.
Depending on your vehicle you may find mods for your stock car stereo, check the net. I know for my car, a 2004 Mazda 3 there are three points on the factory CD player that you can solder in a line in cable! Therefore, no need for an FM transmitter or modulator or any other expensive alternative.