I managed to get the contractor I am working with  (Robert Valitutti of P.C.L. Interior & Exterior Finishes http://www.pclfinishes.com/) to agree to installing R22 under the new siding. Work is in progress as I write this.

The insulation is Roxul (mineral) insulation. There is 2 by 6 inch strapping attached to the brick. Given that there are termites (and carpenter ants) in my neighbourhood I insisted on all wood being treated  with insect repellent. He is using Blue Wood … the “Blu” is a brand name.Strapping on brick wall

After the strapping and insulation are installed he will cover it with Typar (a vapour barrier) and finally the James Hardie fibre cement siding.

The problem with using 2 by 6 strapping (to handle the R22 insulation) is that it could be too heavy to support the siding. He resolved this problem by adding a bottom plate which will support the strapping and keep the siding from being in contact with the ground.
Bottom Plate

Another problem – there is insect damage to the wooden addition at the rear of the house. There had been a leak in the roof that had gone undetected – inviting insects to do their thing. I wanted all of the siding removed right down to the existing frame in order to determine the extent of the damage … it was not pretty. I wanted any damaged wood replaced. 
Existing frame

This is happening right now. After the wood is repaired (the existing 2 by 4 is being replaced with more Blu wood) plywood will be added and then more 2 by 6 strapping and R22 insulation. The result will be that the addition will have R39 … R19 on the interior of the plywood and R22 on the exterior.
back_addition

Removing the existing siding exposed a few gaps in the existing interior wall which explains why there were drafts there.

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