Hiya Guys,
Let me first state publicly that I'm a Windoz guy (GASP!...Run Away!)

OK, for years I've been using the iAudio X5 as my portable player. I chose this primarily because it plays FLAC files natively (is that a word?). Over the weekend when I was cutting the grass my player finally died. The hard drive locked up.
For a while now I've been considering an iPod Classic (160gig) for a couple of reasons. First I've got the iFi chair which has an iPod dock. Next, last fall I installed a new head unit in my car (Pioneer AVH-P5200BT) and on the front face is a USB connection that directly controls an iPod.
Since I really don't want to convert all of my files to mp3 or AAC (I want lossless on my iPod) I considered using RockBox which replaces the iOS on the iPod
http://www.rockbox.org/wiki/IpodFAQtrouble with that is, I suspect that if I install it, I'm going to loose the interface to my head unit in my car.
So, as I'm doing some more research I find out that there is a FLAC plugin for the iPod
http://hammockdistrict.com/flacplayer-faqs/It looks pretty promising.
Getting to my questions. Please bare with me as I'm a complete nubie to iTunes and iPods which makes me an iDiot

1) It looks as if I need to install iTunes first to get the Hammock FLAC Player installed....right?
2) I've seen what the file structure and naming scheme is like in an iPod an it's flippin' awful (or at least it was on the one I saw). Is there any add on program that would simply let me drag and drop entire file folders (with all the songs) without having to go through iTunes yet would still be recognized by the iPod?
3) Have any of you tried the Hammock FLAC player in an iPod? Did it work seamlessly?
Thanks in advance
