This is very good idea for a map -- two-player games are interesting because with the secure +3 autodeploys you always have a chance to catch up even if you fall behind a bit, whereas on most maps once you're down by a couple of territories the difference in deployment becomes decisive.
One thing you might want to reconsider, though: the starting positions differ significantly. Each starting position can directly attack one plane and one tank (let's call them "DA" for directly attackable). But some of the DA planes can be attacked from opponents' DA tanks, some can only be attacked from their own DA tank and some can only be attacked from non-DA tanks. That makes it more or less difficult to attack them. I've played two two-player games so far and won them both partly because I was able to attack my opponents' DA planes from my DA tanks but they weren't.
It's OK to have some degree of variability in the starting positions, so this might be an intended feature; just thought I'd point it out.
Anyway, thanks for a great map!