Wow, missed your response to me from before Jinx1527!
That’s a very good point re winning the SCW before/after Germany is at war. That also plays a large part into the effectiveness of planning. My points towards having a Nationalist Spain so that Italian troops don’t have to amphibiously assault Gibraltar, can also be turned on it’s head: The Allies can then just invade Nationalist Spain, and then retake Gibraltar, also without having to amphibiously assault it! Though, they’d still need to amphibiously assault somewhere on the Spanish mainland as well, and you’re very much correct, Leon-Castille is a prime target. Nationalist Spain would definitely need to beef up defenses on the Atlantic coast.
All very interesting, each part really plays into another part as well in this particular strategy you discuss. I guess you’d need to weigh out what’s more important/effective: 1) Having a Nationalist Spain enter the war, giving Italian troops overland access to Gibraltar, but thus opening up Spain to Allied invasion/widening the defensive window for the Axis or 2) Keep a Nationalist Spain neutral, thus closing easier access to Allied forces to invade mainland Europe, but in the process making an invasion of Gibraltar all the more unlikely again by amphibious assault.
My initial gut response leans with option one: having an activated Nationalist Spain. I think this would, overall, greatly support the Italians more than it would detriment the Axis as a whole. While Spain is now open to assault without Allied penalty, there’s still going to be Spanish troops there to make amphibious landings costly. All the while you’ve stopped, at least for a time, the flow of Allied reinforcement of North Africa/Mediterranean by holding Gibraltar, and/or, depending on how well Italy is doing, opening up the Atlantic to possible Italian interference, if their fleets can comfortably leave the Med.