The OP also said "My main idea is to build something that can function as an entire podcasting website." That's why I started thinking CMS instead of plugin (which is how Loudblog approaches things). After re-reading the (getting long now) thread I see that he is talking about a plugin. But I still don't have any interest in buying a paid service for podcasting.
In my opinion podpress added some big conveniences; the 1pixel-out player, automatic enclosures for iTunes, support for MANY media types including streaming from Youtube, et. al., and even the ability to set a dir as the upload dir and select the media from a drop down (although that is still buggy - it shows an error on the admin page that the path is invalid even when it is correct and works well).
It also has many rough edges, stats are buggy, IE crashes often (many WP blog sites are run by people who prefer IE and don't know PHP or HTML), etc, etc., and the biggest source of this buggyness is probably from the author trying to cram the functionality of his plugin into paid sites like Podtrac or Blubrry. In my opinion simple is best - especially when complexity adds bugs!
Podpress has a great following - I have 4 sites runnning it now held together with patches to the code. But Dan lost a lot of credibility when he promised to release an update for 2.6 by a certain date last summer and then disappeared. He lost even more when his whole support forum went down months ago. Even if he released a version for 2.7 there is no longer a support forum. I will evaluate carefully before jumping back on with any more sites. I may switch to the Podcasting plugin soon since that is under steady development/support and may eventually be rolled into WP core (or not).
By the way, since I mistook what sheda was talking about the first time, let me say it this way - There are already paid solutions for podcasting *plugins* for WordPress. Try http://wordpress.org/extend/plugins/powerpress/