If you don't have Internet access in your car, than using Live Sync really doesn't give you any advantage. The main reason I use it is I have a talk show called "Armstrong and Getty" which starts at 6:00 am and ends at 10:00am.
I record Armstrong and Getty on my home computer using a program called Applian Replay A/V. It saves the recorded web streams in 30-minute increments.
When I start my commute at 7:00am, the show starts transferring to my CarPC from my home PC via the Live Sync. It takes about 10 minutes per 30-minute incremented file (about 13mb) to transfer over the Verizon EVDO.
So I can start listening to the show at 7:10, skipping commercials, etc. By the time the first file is complete, the second one is already downloaded.
The only pain in the butt factor is that Roadrunner does not automatically add the newly downloaded files. So as the files download, I have to go into Roadrunner and add them to the playlist.
When I go to lunch the remaining files download, and I listen to the rest of the show on my way home from work.
I love Replay A/V!
I record Sirius Radio. I switched to higher bit output and sounds great! I record and I record some OTA local radio.