I've learned a lot since that first post.
security chief - Yes it stacks. +10 for each
minister of energy - Yes it stacks, 250 energy and production cut by 50% for each. Probably tactical suicide.
engineer's global effect - Global and in person effects both stack. 2 engineers in a victorious combat recover 100% (less some for rounding) in each combat.
generals' global - Unknown, i haven't tried it (yet) and it's unclear from the description.
tycoon - Yes they stack and man is it hard to get rid of drills fast enough.
I still think most, if not all, of the specialist require description rewrites with strong templating. I'd still volunteer to do it.