Winamp has two bundled plugins that look like they would be really great if they actually worked.

Shoutcast wire: This plugin allows you to subscribe to podcasts. The subscribe part works, but then it falls apart.

• You cannot change the title of a podcast, it uses the title in the feed which leads to...
• You cannot have two feeds with the same title. Therefore if you have two sites which titled their feeds as "Podcast", you can only subscribe to one of them.
• It doesn't actually download anything automatically. You have to go in and select each item for download manually.
• The files that it downloads don't go onto a playlist or something for you to queue.

Portable Music Player: This supports sync and fill of portable music devices. The "Send to *device*" menu item works great.

• I can't figure out quite what the difference between Playlist sync, Library Sync, and Autofill.
• Playlist Sync cannot sync to smart playlists, only static ones.
• None of the sync or fill options can pull from the "now playing" playlist, or from the podcast downloads.

It shouldn't be so hard. All I want is something that will download podcasts, and let me listen to them on the computer or the portable device. What I do is subscribe to the feeds in google reader and save the mp3 files to the desktop, then I enqueue them in winamp and listen to them. Before I go home at the end of the day, I select all remaining files in the playlist and right-click to "Sent to portable". After it has transfered them to the mp3 player, then I delete them from the desktop. Seems like it should be easier.