Recording Radio Shows to iTunes Playlists

[mcs37]

Once I got to Seattle I stumbled upon this awesome radio talk show host, Tom Leykis. But at work I can't listen to him easily when he's on from 3 to 7 due to meetings, phone calls, hallway chats, etc. Being the geek I am, I decided to employ a technological solution: record him at home, and do it cheaply.

I don't want to buy the radioSHARK or whatever that's $70 when a $5 radio with audio out and Wiretap can do this for me.

So here's what I need to do:

1. Hook up a standard radio's headphones jack to the microphone jack of my PowerBook
2. Configure wiretap (or some equivalent program) to record from 3-7 M-F and save as an MP3 (the basic edition I have saves as AIFF, so maybe there is a simple command-line AIFF->MP3 converter other than iTunes out there--any suggestions?)
3. Save each show into my iTunes playlist called "Tom Leykis"
4. Write the appropriate metadata to the MP3 (i.e. Tom Leykis, with a date)
5. Sync with my iPod each night and listen to yesterday's show the next day

I've made it to step 3 but at this point I don't know how to integrate a script into iTunes. I know this is possible since Acquisition does it for me whenever I download a new audio file, but I'm not sure where to look for information on this subject. Can anyone point me in the right direction?

Thanks!

Mike