Make no mistake, I very much respect your artistry. This image is exemplar. The land looks as realistic as plastic topography models that science teachers have. The colored flags make territories unambiguous without having to color the soil. The combination is inspired and strongly crafted. But I have strong doubts otherwise.
The lighthouse is annoying rather than endearing. When I play a map, I study it for three or so minutes. That means it will break my concentration eighteen times. I dread it every time.
The idea was to only have it on a certain % of your turns. Just a simple random generated thing.
This percent idea is unclear. Is the graphic different half the time? Is the drop different, or does this refer to a negative autodeploy on that spot? More explanation would help correlate this to encouraging initiative.
The first thought I had in looking at this map concerned the strong resemblance to a golf course. I have no idea how the territories connect besides those they are next to. Duh? Not quite: if that is the case, the majority of territories are dead ends and sparsely connected. That encourages building because a region is so easily defensible (6 Australias).
I did note the [cannons?] but have no indication of how they work. Since they point out to sea the area of fire is unclear. Do you mean that they can fire onto the other side of the map, on each other? Are they ports, so the regions at least connect on more than one territory?
The number of territory varies widely in each region (1 2 3 5 7

. The larger ought to be well connected to other regions and far from one another. Asia, in Classic, connects on six territories to four continents. Purple seems only next to red and with only two territories close by. Holding the region might be an inevitable kingmaker.
Finally, the alphabet as a naming convention does help. Finding a particular territory is easier than on maps of unfamiliar areas.
I repeat as I began: the map is skillfully rendered. However, its gameplay needs definition.