Are you going with the new Smart Board type siding??? Cause you should it resists rot/mold/and anything that wants to eat it. Never ever go with masonite, it will rot. If your going to tear off down to the stud then chose a good 3/4"-1' foam board. Tape all seams with a good duct tape, no need to buy that high dollar Tyvek tape. Apply that first, then wrap with Tyvek make sure you wrap around corners at least 1'-3',tape well, then apply siding.