I'm with the others on picking fonts for legibility. I know that doesn't leave as much room to show your imagined map-maker's personal style, but it's a trade-off.

I feel your pain about going to great lengths to create detail, then covering it up with text! It hurts, and one feels like valuable data is going missing. Painters do this all the time though, and I understand the value. Say you've put in a background mountain range, and go to paint a foreground tree that covers much of it. The value of the obscured parts of the mountain is in how they make the visible bits hang together as part of a coherent whole. Same way with map details - particularly for a fantasy map. The thinking that goes into the worldbuilding process is valuable even if some of the invented bits don't make it to the screen or the paper.

Now, for some map styles one CAN set down some labels early on... I freely admit to placing some cities and borders where they don't interfere instead of some rational choice of "right THERE at the river join" or the like :-). So your thought of labellng fairly early makes some sense. Even then, SoMeThInG is going to get covered up. <shrug> You could always create a whole series of maps using the same base outlines. The physical topography or satellite view could have minimal labelling. The strictly political map could have little of the topo data but all the city, town, and village names. A different political map might be needed to show area-type info, say if your political units were as scrambled as 17th-century Germany. Then you could do a climate map, a population distribution map, a trade-route map.... sorry; now I've got you making a whole atlas when all you may have wanted was a single sheet :-).

Heh - one can also make a virtue out of a (perceived) flaw -- use lettering to help cover up places you need to stitch tiles together :-).

Your map itself is looking really nice. Some characteristics are sending a mixed message though. The ice just in the north kind of says the map is a couple of thousand miles across, at least. The mountain and city and forest make it seem at most a couple of hundred miles across. And the coasts at the south, where you have the "beach-like" thing going on, make it seem like the whole thing is a few miles across at most. I suppose coastal plains could be ten or a hundred miles across and be mostly sand and dirt, but it's not what I would expect.

You've got what's referred to hereabouts as a river violation. Basically, a lake will have only one outlet. If one point is lowest, that's where water will flow out. Even if another spot is temporarily *exactly* the same altitude , one of two possible outlets would "win" by erosion in a very few years, leaving a single outlet.

Don't take any of that as negative criticism - you have something nice going ! Oh, and you deserve a bit of reputation for being willing to jump right in with a map in the first post - good job!