Audi is into podcasting and he says it's very frustrating to get podcasts on all the available sites. He found a cool plugin called "PowerPress." He says it lets him control cover art and print tags in iTunes. It gives full control over a podcast feed. Leo says it's a great plugin, but it doesn't really work inside WordPress.com. He'll have to run his own, hosted version of Wordpress. But it works great. Another alternative is LibSyn.
The problem with podcasting is that it takes so much to get it from the host to the device to listen to it. That makes it harder for the little guy. Having your own app is the best way to make it easier on your audience.