Yes, I have to agree with Jimson. If the war is won, the fields would be able to reset in the Custom Arenas but I don't see anywhere possible to load multiple terrains to randomly select. However, in the Axis Versus Allies or Special Events arenas that are hosted on the HTC servers, that possibility might exist.
The problem for the Axis Versus Allies and Special Events, has been the inability to control what field and field conditions will exist on the "next" terrain to load. It works for the MA, because each map is configured with 3 countries and all planes enabled. Possibly in the future new tools will be added to allow custom terrains and fields to be loaded in a predictable manner. This would indeed present many opportunities for automated battle series.
As it is the folks in AvA, Special Events and Custom Arenas do an amazing job of creating very interesting gameplay components. A player controlled series might actually be a 24 hour alternative to MA play.