Is it possible or does it make sense for GCC and LLVM to work together? Or does the licensing make that impossible?
There was some discussion of joining forces in the early days of LLVM (ca. 2005 I believe), but for various reasons that did not go forward. Licensing is indeed a big issue: GCC has had the explicit goal of making proprietary plugins technically infeasible, which leads to avoidance of some modularization/decoupling opportunities.