Using mac the ripper: can I rip songs I bought off iTunes and convert to a WAV file for by friend to listen in his car?

I don’t know about that program. But I use Audio Hijack for exactly what you want to do.

It will record any audio as a WAV file. Tell it to record iTunes and it will. It works in real time so you have to listen to the entire song to record it.

I do believe that you can burn your DRM files to an audio cd right in iTunes. This was a few versions ago, and Apple might have changed how their DRM works. Just make sure your burning preferences is set to Audio CD (under preferences -> Advanced). Create a playlist (make sure it is 70 mins or less), pop in a CD, and click on burn.