I’m looking for some help/advice with insulating  my scary wall assembly.
I’m in zone 7a. Northwestern Ontario, Canada right on the coast of Lake Superior. 

My house is well over a century old. In good standing but very poorly insulated. I’ve been stewing about doing some upgrades. Stucco and light mesh was applied to the exterior wood siding approximately 50 years ago and is still in ok shape surprisingly.

Nonetheless my idea was to seal the stucco, attach exterior foam and strap the house and re side it. The main reasons for this is the continuity of the control layer. The other reason is that its just easier for me at this point in time to tackle the house from the outside opposed to gutting the interior.

My wall assembly is attached.

My questions are:
Could I potentially be causing damage to my home by sealing the exterior up in this manner?

If not. How thick of foam and what type?