I love the idea of a strong Italy and especially of exploiting the Greece / Black Sea connection, but your battleplan just doesn’t sound practical to me. Some other commenters have touched on some important reasons why the Allies will almost always win against your Mare Nostrum plan, including (a) Taranto attack drains Italy’s income, (b) UK Atlantic fleet left free to plunder Norway, © high chance of losing battles against UK fleets with so many planes down south, and (d) Moscow is probably safe if you sacrifice that many planes against Egyptian ground units.
Here are two more reasons that I don’t see in the comments yet:
(e) there’s not as much income in the Middle East as you think, especially early on, and
(f) your Black Sea fleet is very insecure, and
(g) Allies can fly fighters to Moscow via the northern route.
So, don’t get me wrong, there’s plenty of money in the Middle East, but maybe not as much as you think. New Roman Empire is 5 bucks, Persian Oil is 6 bucks if you get all three territories, and Egypt + Jordan + Syria + Iraq + Persia = 8 bucks. So that’s 19 bucks a turn. You’re not going to be able to break into Stalingrad / Caucasus money until later in the game, if at all, because there are just too many territories in the way. If you’re taking Egypt on I4, then even with perfect can-openers, that means you get to Iraq on I5, Northwest Persia on I6, and you don’t get to Caucasus until I7. Income you collect on I7 doesn’t help you at all with a G8 attack on Moscow, and if you’re much later than G8, you’ve lost your window of opportunity. At that point the Americans have contained Japan and are pouring fighters into Europe.
So let’s say you collect an extra $19 per turn on I4, I5, I6, and I7. That’s less than 80 bucks. If you throw away 8 German planes to take Egypt (easy enough to do when there are 12 land units defending Egypt), then there’s your $80 right there. You’re not actually making a profit here.
Next up is your Black Sea fleet, which apparently is defended by nothing more than 1 airbase with 3 German fighters. Russia starts with 3 planes. When they see you fly 3 German fighters to Greece on G3, then if they’re thinking clearly, they’ll buy 2 more planes on R3. Those planes will be perfectly helpful for trading and defense of Moscow; it’s a reasonable purchase. Then if you try dropping 2 Italian transports in the black sea on I3, then on R4 the Russians attack your transports with 5 planes, and if you scramble the 3 German fighters, then the Germans lose all 3 planes for only an average of 2 Russian planes, which is fine for Russia.
Finally, taking Cairo and Leningrad isn’t enough to stop the flow of fighters to Moscow. You need to take Archangel, which is not going to happen if you’re buying bombers and sending your planes south. Planes from a London airbase can reach Archangel in one move, and then can fly to Moscow from there – there’s no requirement that Allied planes flow through Egypt / the Mideast.