scripting.com

Please fix WordPress for podcast feeds
  Jay and I use WordPress to do the http://rebootnews.com/ site.
  It's a mixed bag. On the pro side, we both know how to use WordPress, and because Jay writes the show notes and I do the tech stuff, it's a good tool to put between us.
  But WordPress doesn't do podcast feeds well.
  And that's being generous.
  Here's how the UI works currently. You edit your post and link to an MP3 or a movie or an AVI or some other media object. The first one that WP encounters as it parses your text, it will supposedly turn into an enclosure. If you happen to link to two MP3s but the second is the enclosure, you're out of luck. And for some reason if you store the MP3 on Amazon S3, as we do, it usually doesn't even find the enclosure. But this is variable. Today they've hacked up our link to point to some server on wordpress.com, totally without our permission. What a mess. And even so there's no enclosure in our feed for this week's show (which btw I think is one of our best, one I hope everyone listens to).
  For the last three episodes of our podcast, it's failed to add an enclosure element to the feed. As a result none of our listeners get the podcast on time, and it always takes some fussing by the WordPress tech people to get it working, and for all I know a bunch of people never hear the podcast. I suppose it depends on whether or not the client sees an item as read if the guid doesn't change but all of a sudden the item has an enclosure. Imho a proper podcast client would just watch the guid, and therefore would miss the enclosure. Regardless, it's simply unacceptable that WordPress work this way and that Automattic doesn't do something to fix it.
  This is how we did it in Radio 8, in 2002, eight years ago.
  Here's a screen shot.
  Click the screen shot for the full effect.
  See the red arrow pointing to the box called Enclosure? That's where you paste the link to the enclosure. Anyone no matter how technical they are not, could be taught to do that correctly.
  We never had the problem WordPress is having. Granted a lot fewer people did podcasts then than now. Maybe. I'd argue that the way WordPress works now is killing the art of podcasting because it's so unpredictable and it's virtually got the market cornered. Regardless, I'm a paying customer, and I'd like to continue to use WordPress, but eventually I'm going to have to switch because it's killing our product.
  Please Matt and company, fix this!
  PS: I wish Wordpress.com was more hackable, if there was a way for me to patch our feed I could fix this without their help. Alas it's not something I can fix myself and I don't have any interest in running my own installation or fussing around with PHP etc.