I just have a straight-forward question for any who are interested. And it is: where will we be departing from in Skyrim in order to head to Solstheim?
Personally i would assume the player will catch a ride to Raven Rock from an East Empire Trading Company ship near Solitude, considering Raven Rock.. used to be controlled by them. Not sure if they still do, and it's probably safer to assume they don't. However, they may still have connections and a mapped trade route.
Not the most important topic, but with (hopefully) more info about TESV: Dragonborn to come, why not start with the lesser details?