What if you could allow players to trigger game events (just like tabletop), using Computer Version of M44? I'm not a M44 Scenario designer. But if a Scenario included an Area (on the gameboard) allowing players to enter/exit a hex, in order to trigger a particular event.
Example: Air Power card is not playable...If a player draws the Airpower card - then (only then) move unit onto the trigger hex and collect an addition card. If a card is not allowed in the Scenario, simply allow the player who draw's the card, draw an additional card.
But one of the most interesting maps when it comes to medals - vs. victory conditions is Wake Island:
What if we could make it much more interesting? The "Just retreat" you are referring to is the left flank...by no means is it easy. There are five out of six medals on the left flank. This Scenario might be made a bit more interesting; having the Axis player capture at least one additional objective from one or two other fronts (where the was no real way of doing that, there is now)?
Once victory objective is Captured...Move unit (like pressing a button), signifying victory conditions have been met...Manually ending the game.
I didn't fully explain ...trusting your imagination/creativity will take over.