To address your points Grimes:
It would be impossible to NOT know you can/should participate in the base setup. At the beginning of the round players would spawn in a "voting hall", where the only thing to do is run through the voting gates.
"unless the overall path to the flag is roughly the same but the areas that make up the path are drastically different."
That's generally how it would be. The entrances/exits in each "zone" would remain static and the contents would change.
and to explain my magical stickies:
trigger_vphysics_motion that is 1 unit larger than the func_brush, filtered to stickies, with velocity limits set. :>