Static linking as well the REPL are (for me) not the main points on Windows, they might take some more time which is OK for me if else the Windows distribution is in fine shape.
Also not always perfect.
Distribution on Windows (besides static linking) is not a problem. Update: See how this currently looks.
Apple should help with some difficult prerequisites like missing optimisations in LLVM. For more, I think Apple would have to see a clear advantage for them with Swift on Windows.