Hi Folks, I realize I didn't provide an update on how things turned out for my friend... whom I met last month in Barcelona for some Tapas and Beers to celebrate the closing of his second year touring the world in his GS.
So, how did he get to Spain from Alaska? The answer isn't too simple. We tried and valued absolutely everything... from chartering a plane to fly him and his bike (Mucho $$$$), asking a fishing boat captain if he'd drop him off on in a russian port (yes we did), piggy-backing the bike on a private cargo plane doing a refuel stop in Canada on its way to Magadan, and shipping the bike in a container to Magadan from Alaska while flying him to the destination separately.
I can honestly say we evaluated every option and still were not able to find one that made sense for him. This doesn't mean it cannot be done, so don't give up!!!! Just means you need a lot of things to align for things to work out for you, so plan well in advance.
The first option with the charter plane was ludicrous money like Michael said. Bering Air didn't ever get back to me on email, and on the only call I had with them where someone was able to give me a remote idea on cost, they were estimating upwards of $25K to pick him and the bike up in Anchorage or Fairbanks and drop him off in Anadyr (I think)... still waiting for them to send the email quote!
Someone at the Anchorage airport said to talk to the fishing boat captains, so I did. I called a couple, and while the first two laughed at my question, there was one that actually considered it... said it would take a lot of paperwork and wasn't sure how to handle so he had to decline. I am almost certain that if I knew every detail on the documentation side, he would have taken my friend and his bike for very little money.
There was also a suggestion from someone from Russia Air about talking with airfreight/cargo operators in the Yukon that cater to private cargo planes moving oil-rig equipment from Canada to Russia. The idea was to find a plane and captain that would accept to load the bike and drop it off in Magadan. This seemed ideal, but was truly a very long shot and we did not explore further.
The final one was the longer burn and cheaper alternative. Multiple shipping companies could handle the bike from Anchorage via Seattle/Vancouver port in a container, then on thru Busan to Vladivostok, then ferry to Magadan. Airplane ride to Magadan wasn't too difficult either. My estimation was around $4500 to get the bike there and $800/1200 airfare. The problem here was time... no less than 45 days of transit to get the bike delivered door to door (wihtout any hiccup). More reasonable to expect 60 days than 45. Just too much for my friend's plans.
In the end, and after calling much around, we found that Air Canada had an offer called Fly My Bike running during the summer from 3 or 4 locations in Canada, to several countries in Europe. Ended up choosing the simplest alternative, flying my buddy and the GS from Calgary to Frankfurt. The cost was the most attractive part of this deal... paid $1200 US for his ticket, and $250 more for the bike to travel. Another rider arriving the opposite way offered the shipping pallet at no-charge, and the company that does the inspection prior to loading waived their fee (they like these crazy bastards I guess).
From there on, my friend went around northern europe, down to the Balkans, thru Italy and met me in Spain... he is now in Northern Africa.
So thanks to all for your help and suggestions. May reach back out here once he decides to take on the road of bones from West to East, in case he wants to go from there to the US again. What is most likely is that I'll convince him to go to Korea and Japan instead...