This would require some client modification, but I’m happy to work with you on this.

My suggestion for the initial territory allocation would be something like a “bidding” system. Each player is given 100 units which they can place on any territory. When the turn is resolved, the player with units on a territory becomes the owner - the other player can either loose the units or they could be allocated back into there “unit pool” (this would effect the strategies). This would make the first turn very interesting as you could have a number of strategies,

Try and output bid by placing all your units on a few critical territories.
Spread your units around to try and get as many “non-critical” territories.
Variants of the above.

You could also have a “minimum” number of units per territory required so people don’t just put a single unit on every territory.

During any turn a player should be able to add both “add new units” and “attack blah” orders. They can queue up as many orders as they wish and they will be resolved as needed.

For example take this simple 3 territory game,
Player 1 - Territory A (2 units) and Territory B (5 units), has 10 units in pool
Player 2 - Territory C (10 units), has 20 units in pool

Player 1 adds the following orders to Territory A
- Add 10 units
- Attack Territory C (11 units)

Player 2 adds the following orders to Territory C
- Add 15 units
- Attack Territory A (7 units)

Turn resolution happens in the following order,
- Add units
- Attack resolution (highest ID first)

— Turn Generation Begins —

Units are added and then the map looks like this,
Player 1 - Territory A (12 units) and Territory B (5 units), has 0 units in pool
Player 2 - Territory C (25 units), has 5 units in pool

Territory A attacks Territory B with 11 units,
- Territory A looses 11 units
- Territory C looses 20 units
Territory does not change hands.

Map now looks like this,
Player 1 - Territory A (1 units) and Territory B (5 units), has 0 units in pool
Player 2 - Territory C (5 units), has 5 units in pool

Territory C can no longer attack Territory A as 7 units are not available. The order fails.

— Turn Generation Ends —

Of courses there are loads of details to work out here but I hope this gives you an idea on how you can do multiple things in a single turn.

Hope this helps.

Tim ‘Mithro’ Ansell