Too bad the iPhone makes you get sucked into the world if iTunes – because it sucks.  I knew this going in, but it still isn’t fun when the limitations smack you in the face.

The limitation of which I speak is its inability to detect new files in its directories, automatically update its library database, and make it available for syncing and playing.  I spent a while fumbling around the UI looking for the option to turn it on, only to be ultimately disappointed by a few google searches. 

My initial plan was to take home movie clips (btw, MediaCoder is pretty handy..) and drop them into a directory managed by iTunes so they’d automatically get sent to the phone, but now I was going to have to add additional steps of manually adding the new videos each time they get created.  That’s just too much work and I’m too lazy.

I ran across an app or two that would do this updating for you, but instead decided to go a different route – creating a podcast that iTunes would auto-update and sync to the phone.  Tuesday night I whipped up an ASP.NET request handler (IHttpHandler) to generate feeds based on directory contents.  So now I’ve got the auto-updating capability I was initially looking for: after I create the video, I just drop it into a directory accessible by my webserver and iTunes will pick it up the next time it requests the feed.  As an added bonus, David now has a podcast for family and friends 🙂

Some more details on the code below the break.

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