I use my iPod every day in my HCH, alpine is coming out this summer with a box that will give you full control of your iPod and charge it when used with thier head unit (you can toss the iPod in the glove box and leave it), I for one will be first in line.

in the interim I use the griffin iTrip fm transmitter, that is the only way to get a signal into the HCH without doing what you are talking about. the quality isn't that good but mainly it is for audio books that have been downloaded the the iPod so quality isn't that important.