I haven't tried this, but I also suspect that once you have a lot of code fully matching, it might make it possible to ratchet your way up further into builds that you don't have debug information for, that may have more aggressive compilation options. I am not sure if you would manage to get /LTCG builds fully matching even with this advantage, but it's going to be the best shot at it. You're possibly 90% of the way there already.
And yes if you have a pdb / an Od build then things are much easier, I was assuming arbitrary game i.e. release binaries.
The "knowledge laundering" approach you describe might help in reconstructing headers, class layouts and function names which is a godsend although I don't think it would be enough to get a match. Getting functionally equivalent code is muuuch easier (although there's the problem of "how do you verify that without running every function")