I think it's a great idea -- especially for setting up "historical" games, what with all the great history-based maps on CC. However it could ONLY work with PRIVATE games where each player commits to taking their turns promptly and following the meta-rules, which would be:
1) Whoever creates the game should know (or learn) the historical map/scenario, and choose only options appropriate to the time period and scale of the map (e.g. no paratroops pre-WWII; no nukes pre-1945; only trench warfare prior to WWII; etc... and of course, no zombies!).
2) If you join the game, you must study the historical map/scenario and/or get advice from fellow players while setting up.
3) You must choose territories as close as possible to the actual military situation at the start of the map/scenario.
4) At the "allocation of armies" stage, you must do the same as #3.
5) Of course, the number of territories owned by each player is equalized in CC games. This could be remedied by not fortifying any that don't match the actual history, and having a preliminary series of turns where everyone cooperates to conquer/reinforce territories in order to "make the map match the history".
6) During gameplay, each player should try to (more or less) mimic the actual historical actions of the leaders of their faction or nation or empire... e.g. Nazi Germany would be aggressive; neutral nations would remain passive unless attacked; etc.
This option would be enhanced by using teams -- for example: in a WWII Europe game, Germany/Italy would be one team and Britain/France would be one team... and maybe USSR could team with Spain, with Spain remaining neutral and giving all their new armies to USSR.
I think this would be a good way to play with "alternate history" scenarios effectively.... or to create present-day scenarios. Imagine a modern "Classic" or "World 2.1" map with players for the following nations or power blocs, matched as closely as possible to current geopolitics:
European Union, USA, Brazil, Russia, India, China (those last 4 are called "BRIC" in the news), Islam (caliphate?), British commonwealth; Latin America; African Union; etc.
Or imagine a USA map set in 1861 with territories controlled by these factions: USA, the Confederacy, Mexico, Texas (?), Canada, and native Amerindians. Or the Civil War map with the territories and armies matched to history.
Sorry for letting my imagination run wild...