The earliest scenario date and there’s two way to look at it. If you want to be in the drivers seat be the Axis. But if you want to sit back and relax a bit and have more options down the road be the Allies. However… you have to be OK with the fact you will watch lots and lots and lots of units get annihilated in your first game. But the AI will show you lots of excellent attacking techniques to maximize your turns.
Don’t do just Italy. It will be insanely boring after a while. They are just like their historical versions - terrible plus weak.
Not yet I don’t think.