I'm goingto record a podcast about my ideal MP3 player later, but I'll write about it here first. 
I started listening to the Calacanis, Rojas and Winer show late last night. Got about half way through. Put it on this morning only to remember it was strong panned left and right. Sorry, but it's 9am and I've got a headache - having Dave Winer blaring through one ear and Jason blaring through the other was too much. 
So, I haven't listened to the whole show, but I'll say this.
I think they downplay the quality of the iPod. I've got an iPod and a Palm TX. The Palm has wi-fi, Bluetooth, reads SD cards and there is a piece of software called Quick News available which lets you subscribe to RSS feeds and downloads the enclosures.
My Palm Pilot seems to have all of the things which the Winer-Rojas-Calacanis plan seems to ask for. But I still prefer listening on my iPod to listening on my Palm Pilot.
It's not the hardware. Wi-fi doesn't matter - what matters is software and the playing experience.
The whole thing about podcasts for me is that I've got hundreds more than I can ever listen to. This doesn't bother me - scarcity is for atoms not bits, remember.
It means that when I'm walking down the street, I've got more choice in entertainment than I do in breakfast cereals.
The one thing which keeps me an iPod customer is that if you are listening to a podcast and you stop it half way through to listen to something else, when you come back it starts playing from where you left off. If an MP3 player does not have this functionality, it is totally useless for me.
Dave talks about "getting run over" while using his iPod. Sorry, but I don't get this. He seems to want an MP3 player that gets rid of the nuisance of - er - choosing what MP3 you want to listen to. Dave, if you are using the iPod, you can always set up a podcast playlist. Here's how you do it:
Go to File > New Smart Playlist. Now set the following options. Tick the first checkbox, choose "all" rather than any. For rules, you need "Podcast" "is true". Press add. "Play Count" "is" 0. Add another: "Kind" "contains" audio. Now hit "Live updating" at the bottom. Push OK. Give the new playlist a name (I like Unlistened Podcasts). Now go to the iPod preferences and make the playlist sync to your iPod.
You might want to add the "Date Added" column to your Unlistened Podcast playlist and sort that in ascending order.
Now when you want to listen to podcasts, all you've got to do is load this list up in your iPod, press play and start listening.
If you don't like what you hear, all you've got to do is press next (this will not mark it as listened, which means you can listen to it later - if you want to mark it as listened, just fast forward right to the end of the track and let the last few seconds play out.
There you go - it's a River of Podcasts. Takes all of three minutes to set up.
The broader point that the Winer-Calacanis-Rojas thing brings up is perfectly valid. Apple should talk to users. They really ought to let the iPod division's employees run a blog. The people who run the Apple blogs and hang out on Mac forums may find speculation and Apple 'inside baseball' stuff fun and interesting. I find it dull 98% of the time and infuriating 2% of the time (the infuriating bit is when my Mac is doing something stupid and I go in to an Apple forum and the only response is it's supposed to be like that).
What Apple needs to understand is that there's more to this game than just making the product - listening to the customers and saying occasionally, "you know, you're right about that - we're going to add that feature to the next version".
Apple's support used to be the best around - when the European tech support was based in Ireland. I actually looked forward to calling Apple's tech support in Cork. They then moved it to India and it's got a lot worse. If only the person in charge of that decision had a blog and asked the readers to comment.
To conclude: the hardware isn't very important in an MP3 player. The software is what matters. Apple have got the software right in various ways, but there is still scope for improvement. Make synchronisation work with multiple computers. Put the podcast database stuff on the player and make it so yo can hook the iPod up to any device that has an Internet connection. What would that involve? Writing a software update and releasing it to the user - and making a few USB cables so that one can attach it to devices like mobile phones, Palm Pilots etc. Maybe make a little wifi card that plugs in to the bottom of the iPod using USB.
