ZRocker,
In regards to the Handheld stuff...
I cannot replicate items 1, 2 and 3. This may be a hardware issue. I will test with some more players, but I tried two and everything worked well.
In regards to item 5, I think the message does what it should, which is report that there is a problem until it is resolved. After you see the message, you can delete files from the queue and make the problem go away without seeing the box reappear. If you still feel strongly about this, this is an easy change.