As a new owner of an iPhone, I am very happy with the whole experience. The device is great.
As a media geek, I’m finding it difficult to something basic. And Apple seems to be working against me. Here’s what’s frustrating:

I want to be able to update the media on my iPhone over-the-air. I want my Podcasts to be updated automatically, without having to sync with my PC. I also want to be able to email radio shows automatically recorded as MP3 files (using Replay A/V) to my iPhone, and then play them. (Think TiVo for the radio – on your phone!) For me, this would be the coolest. But no luck 🙁

On the Podcast side, an app called Podcaster promised to do just that sort of thing, but was rejected from the Apple store for no apparent reason.

On the Radio show side, Replay A/V is able to send me emails with links to download radio shows automatically recorded by my home PC. I was hoping to be able to send myself radio shows to listen to on my iPhone. But alas, Safari is “unable to download” files from these links. (The links are generated by YouSendIt, which is integrated into Replay A/V).

So, here are my theories:

Stupidity: Is Apple so dumb as to disallow significant over-the-air media transfers for no good reason?

Evil: Is Apple disabling this capability in order to enable their own service?

Weak: Is Apple being bullied by AT&T to disallow too much 3G data traffic? (Another app that let you use your iPhone as a laptop modem was also killed by Apple.)

This is also puzzling given the Pandora player, which is also a media downloader, and works great on the iPhone. There’s no way Apple could kill the Pandora app though, as it would create a huge outrage.
These uncertainties should be troubling to anyone seriously considering developing media enabled apps for the iPhone. And the authoritarian, opaque, random policies behind the app store really need to end, otherwise all the development talent will go to Android or some other truly open platform, the coolness of the iPhone notwithstanding.