I don't see why people dislike the Zune software. My only complaint is that it takes a bit to open. Other than that, I've had 0 problems with it. It looks nicer, runs faster, and is easier to use and figure out than iTunes ever was for me (which was ugly, bloated/ran slow, and is too complicated for its own good, considering it's an Apple creation). I'm no fanboy of the Zune, either. I bought it on a whim (woot.com) and sold my iPod shortly after.
As for the 3.5mm jack, I find it easier to use my Zune via 3.5mm than controlling an iPod through a headunit (at least the model headunit my girlfriend has). With the Zune, I can bring it up to my face so I'm still partially looking toward the road. With the headunit, the screen and controls leave a lot to be desired and are much harder to use than just working straight with the device itself (plus you have to look away from the road, unless you're really good at messing with it). Sound quality is the same either way, though.
Keep in mind, I only used one type of headunit. Yours might completely change how I think about it. You might also really love iTunes, and that's great for you. Use what you like.
Oh, I also forgot to mention that the iPod classic seems to be generally slow/laggy compared to previous iPods. That shouldn't be a deciding factor, but I found it annoying (even after the updates to the iPod).
Really, though...if you like iPod, just stick with it. For your purposes, just use what's easiest and most convenient for you. In your case, that looks like the iPod works for you.
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