Since I already have all of my music loaded in iTunes I would like to put selected artists and/or albums onto a USB drive in as lossless method as possible for listening in my TL when I don't have my iPod with me.

What is the best way to accomplish this? I checked and Windows tells me that the files are currently in mpeg-4 format.

Thanks for any advice.

 

Check out Media Monkey. It is very powerful for manipulating libraries, transcoding files, etc.

 

Thanks for the tip but after reading about all of the headaches with trying to organize the USB drive I've decided that a $40K automobile can easily justify a second nano that I can easily keep current on iTunes and works best with the User interface.

 

My solution to this was done in a few different ways, but the most applicable was with this:

I have a good home internet connection (30mb down/3mb up).
I have an iphone4 with unlimited 3g data.
I have a static IP address.
I have a good firewall.

I purchased a Synology home DS111 NAS server. This is a case you drop a hard drive into, attatch it to your home network, and use as a server for your files. It offers built in application support for iTunes, and also allows mp3 streaming through it's own engine, including the iTunes directories.

The apps for the iPhone are free - which allow you to search your whole music library, build playlists, and stream at full bit-rate, without ever having to copy any of your music to your device. Basically, if I can get even EDGE connectivity, I can stream MP3s right from my home server in full audio quality.

It's all done via bluetooth audio - so no wires. It also doesn't impact the phone connection to the car, so incoming and outgoing calls share the audio with the bluetooth streaming.

It is very stable and works very well.

 

I looked at doing this too (USB) but ultimately ended up digging my old iPhone 3g out of the drawer, reset it and synced all the songs and now I just keep it permanently plugged in the car and just periodically sync up new songs.

You can probably find a used ipod for cheap, something you wont care about sitting out in the freezing cold or heat or if you kill the battery by having it start and stop charging everytime you start the car.

I found the Bluetooth Audio works quitewell with the iPhone 4 (can even advance songs, etc). The quality is not quite as good as being plugged in and it also doesn't display the songs on the screen but still a relatively "clean" alternative as well.

 

Assuming that it works with the car, the new iPhone IOS (version 5) that is coming out this fall is supposed to send the track information with Bluetooth audio. We'll see for sure when it comes out.

In the meantime, +1 for throwing an iPod nano in the car rather than arguing with the phone to get it to work right.