Salute Miska
Your idea sounds interesting, but there are a couple issues which make it perhaps impractical.
First of all, you need guys who would be willing to drive PT boats all the way across the map... not too likely, considering how long that would take.
Second, there are a lot of guys who won't touch a bomber with a ten foot pole... ;
However, my criticisms aside, there is a setup which would have similar concepts which I have being dying to do, except I don't have an appropriate map.
That would be the Murmansk Convoy route over the top of Norway and to the Russian port of Murmansk.
This came under attack from German aircraft, submarines and surface ships.
Aircraft such as the Ju-88a, Me109E, Me109F and the Me110c were heavily involved.
On the British side, they had Sea Hurricane I's, (Hurri I's), Sea Hurricane II's, (Hurri IIc's), Martlets. (F4f4s's), as well as various torpedo and dive bombers which could have the SBD and TBM subbed for.
We would need a map which showed the Northern coast of Norway, Finland and Russia, extending out into the Artic Ocean.
Here's a map which shows the area:
http://www.armed-guard.com/pq17lg.jpgAnd a picture of some Ju's attacking.
http://www.oldgloryprints.com/Arctic_Encounter.jpgYou might even find the map used for a Scenario if its nice enough...