I don't want to put you off, so please take the following only as some tips and suggestions:
I'd reconsider about landing in the UK (Ireland might be better, but very few big bikes there). You are going to need insurance on top of the import paperwork. In the UK, HM Customs and excise are very (stupidly) strict about such things and UK insurance companies are rip off merchants and idiots who won't insure you without a permanant UK address.
I'd aim for Germany first, they are much more efficient and flexible in such matters and there will be no real language barrier in any of the major cities. Once you are on the Autobahn you are free to go anywhere you like in the EU, including the UK.
If you do come to the UK first, get your insurance sorted before you land. If your US company will issue a green card that's the way to go.
The trailer BTW might cause you hassle in Spain and Italy. The locals aren't allowed to tow with anything smaller than a car. Telling Franco trained goons they can **** off as EU law supercedes Spanish law isn't fun.
Andy
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