I recently got an iPhone.  Cool piece of hardware and a lovely system design.  I was hoping that finally I could carry a single device for phone and podcasts, but what a disappointment!

There is a particular podcast that I like.  It is about 50 minutes long, and I have a 25 minute commute each direction.  The show appears on the web site about 2pm every day.  Sometime around 4pm I download the podcast, transfer it to the player.  I listen to the first half on the way home, and the second half on the way into work the next.  If I happen to be home at 4pm, I use my home computer, and transfer it to the player.  If I am traveling on business, I use my laptop, and transfer it to the player.

Can I do this with the iPhone?  Noooooooooo.  I get this:

You mean I have to delete all the FREE podcasts on my iPhone, so I can put one more FREE podcast on my phone?  What a pain!  Sometimes I retrieve podcasts at home.  If my iPhone is synced from home, then when I am at the office I am stuck — I have to drive home to get the podcast for the drive home.  Or, if I sync at the office, how then do I pick them up on the weekend?  Never mind picking up a podcast while on a business trip.  I could always sync to the laptop, but that is a company issued equipment and I can’t install iTunes on it.  This idea that you can sync at only one location is so broken.

So my friends point out: you can download directly to the iPhone!  So at 4pm I check the Apple Store and today’s show is not there.  It seems to take too long for the Apple Store to find out about the new episode; they only have yesterday’s show.

Research leads to conflicting reports.  WinAmp is supposed to transfer to an iPod, but other reports say the iPhone has tighter security that prevents this.  I have not tried it yet.  There are some sketchy sounding software brands offering solutions.  Other places offer solutions if I JailBreak the phone.  I thought the iPhone was supposed to make my life easier!   I am sure I will eventually find the right software. (suggestions anyone?)  All I want to do is listen to a podcast on my drive home. 

This feels like a brand new cool car, that you have to hotwire every morning.

I realize that synch-prevention is a feature of iTunes designed by the lawyers.  But why prevent synchronization of free content which it knows is free because you downloaded it from the Apple Store — for free?  And what about free content from Jamendo?

You can bet I won’t be giving up my MP3 player any time soon.  It is just sooooo much more convenient.