Hey Freodin, thanks for the quick feedback.
I actually have thought through most of the points you bring up, and can satisfy most of them by providing some background on the setting. My friend and I created this essentially as a way to combine all sorts of anachronisms and I then have been further developing it into a setting for a D&D campaign I intend to run. The world is on the inside of a hollow sphere with earth radiating outwards from the sphere in every direction (the earth is interspersed with water and magma, and the occasional cavern. This is in part why there are so many inland seas and lakes on the map - the connect down to deep reservoirs of water "outside" of the world, so to speak. In the center of the sphere is another sphere, which we may call the moon, which is solid. It radiates a gravity-like force outwards, thereby keeping people / animals / etc. anchored to the interior of the large sphere. Around the moon orbits a sunlet. It always stays in the same plane relative to the moon. This relates to the map as follows: moon is directly over Yeni Demirshehir, and the plane that the sun orbits on is perpendicular to it (this is no accident - the city was founded here for religious reasons). The entire sphere is thus bisected by the solar plane, creating a natural division of hemispheres for the otherworldly cartographer. Additionally, each of these two hemispheres have natural poles - the points directly under the moon and perpendicular to the solar plane. The directions on the compass rose are arbitrary; they point to four locations equally spaced around the globe which were decided by League geographers (the League of Guilds being the "Viewpoint Civilization" of the map) as navigational references. Though there is no magnetism to draw compasses towards them, they can be triangulated by explorers who know the position of the sun and their own position, or who can find familiar landmarks on land curved "up" from them. I could have named the directions anything; I stuck with North, East, South, and West so as to try and avoid overwhelming my players with too much new terminology and thus increase their immersion.
As regards the mixing of styles: this was intentional; I think it helps speak towards the anachronistic nature of the setting. The mountain lines and isometric trees and dunes I was particularly worried about; I thought they might not look good next to each other, however, once I had them both on the map I thought they looked fine. Though they might be from different time periods in our world, I have no problem thinking that the people of this world have different conventions in cartography.
As for why a fantasy cartographer would include outdated ornamental ships on his map, I think the best answer I can provide is that Mr. Henry Zorn is a nautical history buff and enjoys illustrating them. I admit, the ships being from different time periods also bothered me some, however, I think they help imply the anachronism of the setting, and that they also add something to the map.
Attached is a scaled down map I have hastily illustrated in MS Paint to try and convey visually some of the information I mentioned in the first paragraph.
-Seleucus
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