Actually when a server is won, all the gains you had are effectively over. Its the legacy awards and prestige that you carry over (see medals) that are persistent from server to server. So no, a dreadnought player does not have another dreadnought on the start of another server. There are some early boosts to players who stick it out through the entire season, for the next server however. There are sooo many dynamic things that I have still to explain, such as ship production limits -- one way to keep from having 100s of people from running around dreadnoughts is that the higher tier ships only get built every so often -- so things like dreadnoughts only come online once every week (so you'd have to be in queue for one if one isn't available). On the other hand, ships like corvettes, frigates, destroyers are unlimited. Realistically, near the end of the server, there wouldn't be more than a handful of top tier ships out there.