iPod Manager (formerly or possibly still known as foo_dop) is a plugin for Foobar2000 which used to be quite well regarded (mainly because it was really the only alternative to iTunes) but it’s not received an update in four years… caveat emptor, as they say.
On top of that, iPods are difficult to justify nowadays… My old iPod was a 60gb model which was ginormous at the time… but now I have twice as much capacity in an SD card that lives inside my Android phone. Time moves on. I took my iPod to bits in the end to replace the HDD and never put it back together again, because it dawned on me that I didn’t miss it. Carrying a battery-powered device with a spinning hard disc inside it, explicitly for the purpose of playing music… seems as old hat today as going round with a cassette player strapped to your butt seemed when we were all going nuts buying iPod Photo. (For the same price that today can get you a Samsung Galaxy… You feel old, yet? I do… I’ve still got a Walkman in the cupboard! 😉
I use it. It’s confusing to use at first but I’ve never had any issues with it outside of that.
Now THAT is a good idea. I’ve got my phone with me 99% of the time so I play in-car music from that, but for those emergency occasions where I forget my phone or it’s broken or something… I keep a clapped out HTC Desire in the glove compartment with about 40gb of "emergency" music – God forbid that I should have to put the RADIO on… 😉