I've just downloaded this map and briefly taken a look at it.
Firstly, let me congratulate for the over 180 thousands visualization of this thread so far (coming from someone whose main map thread has not even reached 1 thousand as of yet).
I understand that the HQ are never going to be very good depictions in the moment you have to have one dude's face for all land, sea or air, but I find the Italian ones particularly bad.
For the land, you have used the image of Mario Roatta, who starts being very important only in 1942 and only about commanding the anti-partisan warfare in ex Yugoslavia, something which is not even depicted in this game (unless I'm missing some rules), so we have an image of someone which is not even where that guy was at the start of the game and is not going to be pictured in this game anyway.
Instead, I would suggest to go with an image of Ettore Bastico, not because it is considered a particularly good general, but because the Italian HQ-Army in North Africa is headed by him.
For the air, you have used the image of Italo Balbo, who died on 28 June 1940 so is barely a World War 2 figure at all (having died of friendly fire 18 days after Italy entered the war)...
Instead, I would suggest to go with an image of Francesco Pricolo or Rino Corso Fougier, respectively the head of the Italian Royal Air Force before and after November 1941, November 1941 being the month when the former is substituted by the latter.
For the sea, you have used the image of Pietro Badoglio, which makes absolutely no sense because he was not even an admiral. Seeing Pietro Badoglio smiling over the sea at the command of fleets is terrible and arguably the worst thing in this game of all the pictures.
Here the image has to picture Angelo Jachino.
About the Germans, talking only about the land HQ, I guess Rommel is fine, but it is really weird to see Rommel everywhere (especially on the Russian front) in the moment he is a figure strongly identified with the war in Africa (Obviously, he was not in Tunisia at this time. I don know why any German unit would be there.), which was enourmously less important than the Russian front.
I would have rather gone with the Manstein picture which @Black_Elk provided, although he actually never took part in main operations during 1941 and 1942 (In 1941 was in Group North, which was the least important of the three groups, then in Crimea, which was a side-show, then again back to Leningrad thereabout, again being the least important front beside anything farther north.).
For the HQ in the way it is used here at start game (3 German HQ being present on the German - Russian front except Finland), I'd see the HQ as representing Army Groups, so I would go with an image of Fedor von Bock since he was often the commander of the most important group until he was fired on 17 July 1942, and in particular commanded Operation Typhoon, arguably the most important late 1941 operation.
An other lower level possible pick would be Heinz Guderian, who actually started Operation Barbarossa serving under Bock, but the main problem with this is that historically Guderian had a very long hiatus starting on late December 1941 (so it would make little sense to see him anywhere during 1942).
A possible alternative, strongly related with both Bock and Guderian, would be Maximilian von Weichs. He took the 2nd Army command from Bock and then again took over for Bock when Bock was dismissed (this time leading Army Group "B") so serving directly under Bock until taking over for him for all the war with the Soviet Union. I would say that for a 1941 game this is not as much a good pick as Bock, but it has the upside of making sense still to see him around in late 1942 onwards, even though he would be eventually relieved of command in favour of Manstein when things started to get very ugly.
On a dynamic perspective, starting in late 1941, I would say that (in this game) the German HQ image for land forces would be better as initially an image of Fedor von Bock, then substituted in July 1942 by an image of Maximilian von Weichs, then substituted in November 1942 by an image of Erich von Manstein, then substituted in April 1944 by an image of Walter Model.
Long story short, I'd substitute the image of Rommel with either Manstein or Bock.
Something I cannot understand is why having an HQ-Submarine image on the sea depicting Karl Dönitz in the moment he was obviously never actually commanding the submarines from the sea? Is the HQ-Submarine supposed to be on a submarine?
Generally speaking, I think that the HQ images of this game are questionable, so I suggest to reconsider them all.