soxprospects.com has a good podcast that they put together... once every 10 days/two weeks. Heavy on prospect talk... they're pretty comprehensive, working through each level in the organization, college draft, international free agent signing period, individual player profiles. Somewhat technical in the discussion. Not heavy on comedy, but they still keep it light.
I like it.
I also selectively download Toucher and Rich, and occasionally Felger and Mazz depending upon day/topic/hour. Rusillo and Van Pelt wasn't bad in their day for a more national take; don't know what Rusillo and Kanell are like now. I recognize these last few are radio shows, but I live out of market, so I access them via podcast and listen to them while I work out or cut the grass...