Hi KCB,
Sounds like an adventure and a half - good luck, hope it all works out
I rode in Eastern Europe this year and the eastern European border guards took the p1ss. I was at the Ukrainian, Serbian and Romanian borders for hours while they went through me, the bike, the panniers and every bit of paperwork they could think of.
The thought of having to be at a certain port on a certain day to catch a boat that might not be there due to weather, etc
Stating the obvious, but you are going to have to think so far ahead for every eventuality.
I'd love to know more about the trip and the route, so if you have some time, fill us in.