But seriously, how often do you have your iTunes set to check your podcasts? And do you have it set to get all new podcasts or just the last one?
Before I got relegated back in to the dark ages of dialup because of my recent move (I haven't used dialup since 1994, woe is me!) I had no problems with iTunes getting my podcasts updates. I set it to check hourly though.
To me it sounds like you have it set to check manually, and that requires your intervention. Try playing with some of the settings. Another alternative that is ok, but not as good as iTunes for podcast management in my books, is J.River Media Jukebox.
Windows. iTunes. Video iPod.
Here's what I want the world to be like: I wake up. I eject my iPod from my computer. All of my podcasts, such as BOL, are on it. They have all been updated overnight and synced to my iPod. I go to work.
Here's what the world is really like: I wake up. I go look at iTunes in Windows. My podcasts haven't been refreshed since I started iTunes last night. If I *didn't* start iTunes last night, they haven't been refreshed since the last time I started iTunes. I click "Refresh" in the podcasts Window. I go brush my teeth or something. I come back. My podcasts are still downloading. I go floss. I come back. They're done! I click "sync". My iPod starts syncing. I go shave. I come back. They're done syncing! I click "eject". I go to work, but my day starts off full of anger and bitterness at iTunes. Consequently, my day is slightly less enjoyable than it might otherwise have been as a direct consequence of technology.
The world is failing to keep up with my expectations. Suggestions, please, on how to make things work the way they really should. Suggestions along the lines of "Don't use iTunes, use <alternative>" will be considered, but I've had some fairly negative experiences with most iTunes alternatives. Suggestions along the lines of "Get a Mac!" should be accompanied by cash donations. Suggestions along the lines of "This doesn't happen to me, you must suck" will probably not be very useful.