Have known of people go to the States, buy a bike and ride it and sell up before leaving, worked well for them. On the reverse met an Oz on the IoM who had come over to Italy to buy a Ducati, rode it out of Italy on temporary plates (as he was supposed to do in Italy) decided they would never be noticed in other countries, so kept them. Rode about Europe looking about and then rode home to Aus.
£500 to ship a £2000 bike is quite good, £500 to ship a £500 bike is bad business.
Cannot remember the name of the org, but we had a Yank stay with us who had a book of addresses (Published) of people willing to give a nights or two bed and board in return for some jobs being done. I was happy with his yarn, but he insisted in doing a load of cleaning even though we were not in his book. He had various things to do, cleaning, gardening, mucking out cattle etc. None too onerous and all stuff he would have done if he was staying. Now if anyone can think ofthe name of the org, they have 'members' all over Europe, US, Canada etc.
Will you be taking a list of useful contacts? I have a Brother In Law who has a motorcycle hire company on Koh Samoi (Thailand) Now whilst you will not be looking to hire a bike from him, he MAY be willing to let you use his workshop in return for some labour on his bikes etc.
R