In my opinion, if you use extruded polystyrene or insulation boards with aluminum foil such as Thermax and then tape the seams, then I see no reason to use a house wrap since air will not penetrate the insulation boards and OSB. House wrap or taping the seams should be enough to keep the rain from entering the wall cavity, especially if you use a positive drainage plane (void) between the siding and the insulation board.
For new construction, I would use windows with nailing flanges. Again, IMHO, I think the flanges of the window should be attached to furring strips that line the opening. Then tape should be appled over the flanges according to a method that leads water away from the window. Hardie Siding is then butted up against the window trim and corner style boards.
Wider furring strips around the windows will be needed in order to support the exterior trim. This means that the window trim will terminate the Hardie Siding.
By the way, try to avoid using wood for corner styling, window and door trim. I prefer cellular PVC. Cellular PVC paints well and will hold the paint longer than wood. (Be sure to clean the PVC before painting.) I believe Hardie has corner style boards available if you do not want to use cellular PVC.
If anyone sees anything wrong with the above ideas, please speak up now before someone relies upon my non-existent experience with weather in cold climates.