The Radio Shark hooks up to my PC by USB and let's me record over the air radio broadcasts in WMA format. It has some software to schedule recordings. Unfortunately it doesn't give you much control over the tags, so I wrote a little VBScript to update tags, add the files to the Windows Media Library, and delete files over a specified retention period. I would say it was fun to do some coding again, but I know that script gets no respect as "coding" from true developers. Maybe someone else will be interested in my script. It would come in handy if you want to programmatically manage WMA tags. Check it out here.
I like the Squeezebox becuase it has a very active user community building plugins. One guy has a plugin that lets you listen to all of the BBC Radio streams, another has a plugin that scrolls news headlines (or any headlines) on the Squeezebox display via RSS feeds. My only complaint is that the Squeezebox has no DRM support -- Slimdevices seems to be philophically opposed to DRM. Kim has bought some DRM'd music from music.msn.com for her Zen Micro, guess we can't play it on the Squeezebox.
They have a wirelese model, but since I already have a cat5 run popping out by the stereo cabinet, I bought the wired version. Only $169. You can control it by infrared remote, or from any computer on your network via a web interface. So I can control it from the new Kiosk PC that sits right in the living room with the stereo, even though the music is all on the PC in the basement.
Now what I <b>really</b> need is a solution for the car. I looked into the Omnifi solution which seems like the best one (it does scheduled wireless synchronization from the garage), but from what I've heard, FM transmitters suck, and my stupid proprietary Volvo stereo lacks auxilliary inputs. I've considered just going all aftermarket on the stereo, replacing the Volvo stereo, but I've read it is hooked into the rest of the car's electronic brains such that this isn't a great idea. Plus I want to keep using the volume and transport controls on the steering wheel. I think I'm either going to have to buy a new car or pray that Volvo releases a new stereo that will do the job for me.