1. We don't silently skip instrumentation. If we can't find a free register then we will force the frame setup code to the front of the function so we can get one. See the diff in PEI::calculateSaveRestoreBlocks().
2. We do spill the calculated value to the stack. This is unavoidable in many cases (non-leaf functions). It would be an optimization to not do this in leaf functions, but this would also mean finding a register that is unused throughout the function. This turns out to be a small number of functions, so we didn't pursue it for the initial implementation.
3. I'm not sure what you mean by the cookies are shared. Do you just mean that they are all in the openbsd.randomdata section? They have to live somewhere. Being able to read arbitrary memory in the openbsd.randomdata section would leak them, yes, though this doesn't seem to have been a problem for the existing stack canary, which lives in the same section. I see that RAP keeps the cookie on a register, which sounds like a neat idea. I'd be curious to see how you manage to rotate the cookie arbitrarily.
4. I'm glad you like the int3 stuffing. :-) We could always make the int3 sled longer if it turns out these rets are still accessible in gadgets that terminate on the return instruction. Have you found any?
Anyway, I'm happy to see your commentary on this. You guys do some nice work! If you have other suggestions for improvement I'd be happy to hear them. You can email me at mortimer@.