This is outstanding work! Very high praises are in order.
A few nitpicks for the map of Estonia.
The prewar and current map have changed somewhat and in a way that this cannot be transformed into HOI or AoD scale. However I suggest that you split thet big province in estonia horisontally.
Here is my two cents to help you (sorry for my lousy paint skills).
The Green area should be province called "Tallinn" in game terms (the location of the city spot is purple).
The Blue area should be province called "Virumaa" or "Narva" and if it has a city centre it should be "Narva".
The Red area be province called "Tartu", city of Tartu is again designated by purple color.
The Yellow area be province called "Pärnu" (or Parnu), city of Pärnu is again designated by purple color.
I would suggest the islands to constitute a fift province, but if this is not a great idea
)) then give the northern one to "Tallinn" and the Southern one to "Pärnu".
If they are a separate province they could be called "Saaremaa" or "Kuressaare" the location of the town of Kuressaare is purple. If the islans form a separate province they should have a land connection (like sicily to the boot of Italy) to both Tallinn and Pärnu.
Also I used red striping for territories lost to Soviet Russia (and nowadays to Russian Federation after WW2 and the occupation). Just as a piece of information to you. If the map is supposed to be mostly for WW2 time period you could make the map reflect them to be a part of Estonia.