2) Talk to a lawyer, anything can get you sued.
In theory Apple could claim trademark confusion between this shirt and official merchandise (of which they have none). It's pretty far fetched, but technically possible. The iPod click wheel itself is patented, but a flat 2D image of it is the same as any other control wheel on a remote: it's just two circles. "Apple" and "iPod" are trademarks, but a picture of two circles isn't.
But if you want legal advice you need to talk to a lawyer - all we can give is two pence worth of opinion. Worth approximately nothing in open court.
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