Trying to make eso map "accurate"

MaisonNaevius

As for the accuracy of the map. Zos modifies and updates it when necessary. Look at the Morrowind area, when Vvardenfell was added, everything was declared a little further east.
Summerset has also been updated.

The Winterhold area is therefore not a problem. It will be a simple update like the two examples I cited.

Note that between the basic zones and the DLC zones, there has been a lot of progress. The care taken is more important. Giving this basic region effect typically MMO and the last regions as worthy of a solo TES.

Varana

The two cities in Middle Elsweyr are probably exactly the reason why it was left out. A zone these days features one major city - in Northern Elsweyr, they went with Rimmen, and with Senchal in the South. They managed to cheat a bit with Orcrest, also a major city but conveniently devastated at this time.
They probably could've added one of the missing cities as a minor city like Balmora or Shimmerene. Unfortunately, Elsweyr was quite stingy with settlements.

I don't think Craglorn can serve as a useful example. In terms of ESO, that is basically ancient history now. Things don't work that way any more.