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| $10k equates to about 13k Swissies; import duties should not apply if you've owned your bike for > 6 months (don't quote me) and the shipping for a bike will be $1000 (guestimate).
I'd assume not much would be needed for roadworthiness - clocks, legal can, vehicle check. Also if the cops stop you and the can is aftermarket, they'll want to see your permission slip.
There's nothing wrong in wearing shorts, flip-flops and a t-shirt - the Nanny State has not made rules on what to wear  Personally I find I crack out the best wheelies in my flip-flops 
I have a BMW R1150R Rockster btw  | |
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Lob rockster you say 1000 for shipping a bike. an how? i here diver and fly with a bike too the eu.