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I'm using Tasker which is in beta and not in the market yet to do just this. In fact, I have a Tasker Profile that when I connect both Power and the Headset at the same time, Tasker will set the Keygaurd (scroll to unlock) to off, then set the screen to stay awake, and then popup a menu of various audio apps that I can select from to launch so I can start playing some audio from the program I select from the list. I could have just launched the music app without prompting a menu of audio apps, but sometimes I select Music, and sometimes I select Google Listen. I also have the enter task toggling on and off the Bluetooth since my car's built-in Bluetooth doesn't connect correctly to my 1.5 Hero, so now that is automatic too. Boy, can't wait for the 2.1 update to fix all the Bluetooth issues on my Hero!!! Anyway, when I unplug the Headset and/or Power, then Tasker runs an exit task to re-enable the Keyguard and disable the stay awake. So, Tasker makes this all automatic for me.

I also have another task for just Power and USB Plugged that runs a task to disable the Keyguard with an exit task to re-enable it. So, if I have my phone plugged into the desktop for charging, the scroll to unlock is disabled. This one is a bit buggy since the developer says that keeping the Keyguard disabled wasn't the intent of what this feature was for, but it works most of the time even though Android tends to sometimes re-enable the Keyguard randomly for some reason.
 
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