I have done most of this trip in various pieces and would very much recommend it - in particular if you have time to visit Newfoundland for a few weeks along the way (it is only an overnight from Cape Breton in Nova Scotia. All sorts of variety to be had. You really do need
radar in Atlantic Canada and Newfoundland is pretty isolated (but fabulous cruising) so you need confidence to be self-sufficient there.
Let me know if you have any specific questions.