There shouldn't be any problems AFAIK. You should check with both your
insance co and the local building department first. Cedar shakes are
banned outright in many places for roofs (I don't know about siding),
Many insurance companies won't insure if shakes are used.
yes, this should be fine. if you are in an area with wind driven rain,
or if the shakes are to be painted, consider strapping them out.
providing an airspace between the shakes and the t 111 will provide a
drainage plane and also make any finish you use last longer. at any
rate, put a layer of building paper under teh shakes.
For siding my house has had Cedar shakes on over siding for 40 years,
they are fine. Maybe for a roof you dont install them over decking but
maybe its just a cost issue. If you didnt put them over wood new cedar
homes would have no wall insulation value
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