Siding and Insulating 125 year old Cottage

6 years ago
We recently bought this 125 year old cottage. The home is in Maine and has been used primarily as a summer cottage for the past 25 years. We plan to use it mostly in summer but some in the winter. It currently has cedar shingles. Three sides of the house the shingles are in B condition, but the front has severe cracking, warping, etc.. We were getting ready to repaint but hate to paint over the failing front shingles.
I assume there is little to no insulation in the walls, however the attic is well insulated. I am considering just replacing the front shingles with cedar shingles, or replacing the whole house with pine or cedar clapboard and using 1" rigid foam under the clapboards. We plan to use a solid color stain. Any advice would be appreciated we would like to keep costs down but do it right when we do it.

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