I've been hosting a weekly show for 10 years, and have used WordPress for about two. I've followed the directions in the Codex to have enclosures done for each playlist posted, and also use a rewrite rule in .htaccess so that each post with a podcasts tag will be seen by Feedburner and iTunes. It's been working well for me.
I thought it'd be neat to install PodPress, as I feel that it's a cool enhancement to my show's site. But the get-go, I've had problems with getting enclosures to work properly with a test post, which was for my most recent show. Though Feedburner was able to find the XML source, it was without a proper enclosure. I've struggled with different variations in PodPress's Podcast Feed URL, but to no avail. iTunes wasn't able to find the show, either; just the previous that I've already had.
Alas, I had to deactivate PodPress. Once that was done, iTunes was able to find the show once I've did the usual WP enclosure in the Custom Field section of the editor.
It would be great if I could get some guidance on how to do this right. I'd like to get PodPress working properly and have both iTunes and Feedburner find the enclosure, and at the same time not break the existing shows that are already there.
Thanks so much for reading; hope to hear from you soon.