You can, of course, connect two Androids from USB to the same dev machine, and you can debug both of them.
If you use adb, you need to specify which Android you are debugging, and can only debug one at a time.
If you use Eclipse (Helios), you can select the device in the Android device view and see the output in the Android Logcat view. And I notice that if you select Android A and then Android B several times, you will get mixed Logcat output from both devices. I do not know if this is constructive behavior, and may not work the same in all versions of Eclipse, but it can be useful.
Another approach is to monitor one device in Eclipse and the other in DDMS.
Torid
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