So long as you don't uninstall TSW6 before installing at least the base TSW7, when you first run the latter it should prompt you to import your profile and information. At least that's how it worked in previous years. Note though it will not transfer across your in game settings, last year I jotted them all down on a piece of paper. What's not clear is whether the Monthly Mastery will roll over from 6 to 7, though that's a relatively minor concern.
It will. My only concern is if DTL will be able to handle all the players playing simultaneously the first few days.