macbook to DAC to server/cd recorder

Sounds like what you're look for is Audio Hijack Pro. This is an app that allows you to record any audio passing through your Mac--a MUCH simpler solution than the one you've proposed.

I've not actually used it, but it is well reviewed in Mac circles, and only costs $32. If you try it, let us know what you think.
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I looked into it and from what I can tell there is alot of compression to the digital content.

From the description of the application's features on the website:

Recording Options: Record to MP3, AAC, Apple Lossless, or AIFF audio formats.

Hmmmmm.......AIFF? Apple Lossless?? These don't strike me as highly compressed formats.
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it will accept all these formats but the end result is highly compressed

For live streams I use Radio Lover, what goes in, comes out, unless you want to change format.....nothing to it really, great for capturing obscure web radio streams and has a some really slick features such as scheduling, auto tag and split tracks on the fly into folders etc.....Which I then burn to disc, transfer to iPOD etc...you can easily record over 10 high-quality 128kbps streams at the same time.
* Record MP3 Internet radio streams as individual MP3 songs
* Songs are automatically tagged with artist, album, radio station and track number
* Schedule recordings of your favourite shows
* Record multiple streams at the same time
* Split recordings by song, time, or size
* Import from iTunes Radio Tuner
* Drag and drop MP3 stations from iTunes and the Web (typically these are links that end with .pls)
* International language streams supported
* Supports thousands of Shoutcast compatible and M3U/EXTM3U style radio streams found on popular sites and in iTunes Radio Tuner
* Wake computer from sleep for scheduled recordings
* Assign custom recording styles for each stream

Audio HiJack Pro is also well cool and does exactly what it says on the website, as REL said above...AIFF is NOT compressed dude !

Also think about what you can hear on the road.Who cares if they are compressed?You won't hear it rolling.Besides I'd get a Netbook for Wav files before I spent more for the Olive unless you really want it.My complaint with Olive at this poiint is you can't control external USB drives or I'd say get Olive as a primary player.
Chazz

I already have the olive but i dont need to use it. It has not been the most reliable. I'll give the others a try but hijack did not sound all that great when I gave it try a while back.