I'd really suggest avoiding doing this. When stucco is installed, any trim boards that the home is intended to have are already in place and the stucco is flashed/butted to the trim. The trim is never installed after the stucco. Too many chances for rotting trim since your drainage plane is the face of the stucco.
If you insist on doing it I'd recommend not penetrating the stucco in any way, even if you use silicone to seal the penetrations. Its just asking for problems.
If you insist on doing it I'd recommend not penetrating the stucco in any way, even if you use silicone to seal the penetrations. Its just asking for problems.