The map has several distinct geographic areas.
Italy, Sicily, Corsica, Sardinia, Tunisia, Malta and Valletta.
Here is how I would place aircraft and vehicles for each geographic area.
Jeep for both sides at all fields
Italy-Axis
Airfields-Ju88, Ju87, 109G6, 190A5,C202, C205
Vehicle- Panzer, Tiger
Ports-Panzer, Tiger
Italy-Allied
Airfields-P40B, P40E, Hurricane IIC, Spit V
Vehicle- Sherman
Ports-Sherman
Sicily-Axis
Airfields-Ju87, 109G6, 190A5,C202, C205
Vehicle- Panzer, Tiger
Ports-Panzer, Tiger
Sicily-Allied
Airfields-P40B, P40E, Hurricane IIC, Spit V
Vehicle- Sherman
Ports-Sherman
Tunisia-Axis
Airfields-109G6, 190A5,C202, C205
Vehicle- Panzer, Tiger
Ports-Panzer, Tiger
Tunisia-Allied
Airfields-B17G, A-20, B25C, B-25H,B26, Boston, P38G, P40B, P40E, Hurricane IIC, Spit V
Vehicle- Sherman
Ports-Sherman
Malta-Axis
Airfields-109G6, 190A5,C202, C205
Vehicle- Panzer, Tiger
Ports-Panzer, Tiger
Malta-Allied
Airfields-A-20, B25C,B26, Boston, P38G, P40B, P40E, Hurricane IIC, Spit V
Vehicle- Sherman
Ports-Sherman
Valleta-Axis
Airfields-109G6, 190A5,C202, C205
Vehicle- Panzer, Tiger
Ports-Panzer, Tiger
Valleta-Allied
Airfields-A-20, B25C,B26, Boston, P38G, P40B, P40E, Hurricane IIC, Spit V
Vehicle- Sherman
Ports-Sherman
Sardinia-Axis
Airfields-Ju88, Ju87, 109G6, 190A5,C202, C205
Vehicle- Panzer, Tiger
Ports-Panzer, Tiger
Sardinia-Allied
Airfields-P40B, P40E, Hurricane IIC, Spit V
Vehicle- Sherman
Ports-Sherman
Corsica and Northern Italy don't really need any planes or vehicles enabled as the fight should be no where near there but Corsica would mirror Sardinia if it was desired to put the aircaft everywhere.
My only question is the C-47. If the Axis push the Allies back into the sea the C-47 should be somewhere to allow the Allied to get back on the island. Either the CM would have to just reset the arena in this case because that is technically a victory for the Axis or the C47 could be put at A25 in Tunisia, allowing the allies the ability to create another airborne assault as was the case on July 10, 1943 but not so close that folks are flying C-47's to capture bases in Italy.
The other question is settings that allow for base capture but make it hard for one person to do it by themselves. I think everyone here frowns upon the army of one capturing bases. My preferred method of achieving this used to be upping the number of troops required to the point the base reopened before a single player could possibly deliver enough troops to capture. This, of course, requires suitable down times