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\Will it be possible to import all existing LW content?
Yep! We have a working import system tested on a partial DB dump Trike gave us. The main wrinkles are around editing old posts--we're moving to a different format from the raw html with an editor (so that comments and posts will have the same editor), and so the first time you edit an old post you might have to do a bunch of conversion work / it might not be possible to get the exact same look.
(For example, I don't think we're going to have font options anymore, and so that'll prevent accidental weird fonts from copy/pasting from another source, but will mean any post that wanted to rely on different fonts will be out of luck.)