Nice work Tjoek!

Small thing: maybe instead of M/m for Industrial Complexes use L/S? The difference right now is easy to overlook if you ask me. And Large/Small should readily translate to Major or Minor right?

Again, you are spreading yourself way too thin here!

S111 = 1 sub, 1 battleship, 1 fighter, 1 tactical bomber

-> Scottish Fighter Scrambles, making it a fight slightly in the favour of the British. (2, 4, 3, 4 against 2, 3, 4 and 4, but you will lose one 4 if your fighter has to go down).
In S110 you are bound to lose a fighter.

Normandy and especially Southern France are gambles and you will likely lose a lot in France itself especially if that AA hits something. S91 is not in your favour either.

Not to mention that in this plan you would be sending 3 German transports without any form of escort down. With the RAF (or even the French fighter from London) looking for every opportunity to take that down, you would only really be safe if you stuck to Italian seas and a scramble there. But then, that defeats the purpose of sending them down in the first place.

Not to mention this would all leave London free to do as it pleases with 2 transports and 2 destroyers left and no real worries about the Luftwaffe which you send down to the Med. And Russia might also just go more aggressive as long as it sees you are not in a position to attack yet and stack on your border.

Do not get me wrong, I favour an empower Italy strategy. But you try to do everything at the same time and that usually means all will fail or succeed with marginal troops left over. The advantage that Axis turn 1 have is a sheer might of numbers. Do not easily discard that in your plans. Overpower, do not go for even fights where the allies stand a chance with a good roll of the dice.

@Afrikakorps:

Italian Builds
I1: Transport
I2: Minor Factory in Greece
I3: Airbase in Greece, 2 Transports in S100
I4: More Troops

Italy Turn 1

Purchase new units
1 Transport

Combat Movement
Greece with 1 Bomber, 1 Tank, 2 Infantry
Yugoslavia with 2 Artillery, 2 Infantry
Gibraltar with 1 Tank, 1 Infantry
Tunisia with 1 Mech, 1 Artillery, 1 Infantry
Alexandria with 1 Tank, 1 Artillery, 3 Infantry
Anglo-Egyptian Sudan with 2 Infantry, 1 Artillery
Kenya with 1 Infantry
S93 with 2 Fighters, 1 Destroyer, 1 Submarine
S92 with 1 Cruiser, 1 Transport (1 Tank, 1 Infantry

Although I have only just registered, your post sparked my interest since I love tinkering with strategies in the Med and the Middle East ever since starting to play this game. This certainly is an unorthodox idea, even for me! 
I do have a couple of questions though. Mainly because you assume both a very passive British player and, it seems, some very lucky dice rolls on your part.

On your first move, you try to take Greece with your Strat Bomber and the troops from Albania. That is a battle of two 1’s, a 3 and a 4 against four 2’s. Not very much in your favour… yet detrimental to your entire plan should it fail. Now you mention you do not like calculating battles, but if I put this one through the calculator anyway, you only have a 65% win. What’s more, the average unit left is close to 1, meaning you will have to sacrifice your Strat Bomber most of the time in order to claim Greece. That does not make for a very good Italian first turn I would say.

Furthermore, you plan to take Algeria, which will by then have 2 French Inf, with your leftover(!) troops from Tunisia: 1 Mech, 1 Inf, 1 Art. Not only is that fight only marginally in your advantage again, this is assuming you lost nothing before. If you did, its at best an equal fight, at worst a French overweight.

There are more examples of this, but you get the general idea now.

Besides this tendency to overestimate your own rolls and underestimate any possible counter moves, you also make some straight out errors. As pointed out by others here, there is likely a left-over British fleet in S97. I assume the Luftwaffe takes this out for you? This does however mean like they pointed out, that you gain less income and cannot possibly build a transport in S97 on I1 right - unless I am mistaken and missed some rule?

Last, I am puzzled as to what Germany does exactly. You mention building a transport on G2. Then how does Germany do an attack on G3 with 4 infantry?