OK
Freddy fair to describe Italy as a boot, but it's a long kinky boot that goes righta upa to her bum! So you send your armada to the Po delta and establish the worlds biggest beachhead. Then you march inland with the enemy below you, and, the enemy above dumping down on you from some of the best defensive rocks in Europe, (Rommel said so

)???
Then, you have to get your supplies up the Adriatic with enemy on your west coast and enemy on your east coast - Tito wasn't that good in 1943??? (wasn't that good after but there you go).
You want to land from the Med? Got to be Genoa or you're straight into the mountains??? So how much can you cram in at Genoa, (Dieppe ring a bell -
dunggg), and where you going to go from there? Only one passage to Alessandria??? Tight!!!
And, as
Erich pointed out, where's your air cover coming from???
No.9