Alright, to be completely honest with you this map is way to huuuuuuuuuuge to depict Iceland properly. If you're on your way using a random generator I expect this map to contain more fictional material than it does realistically. Perhaps I would question if this is going to be a real-life map after all? Iceland is a very sparsely populated country with almost half of the country living in the capital, Reykjavík. There isn't much elsewhere in the country other than some fishing towns on the coast. But don't be fooled, move to the inland of the country and you'll see almost no towns at all. Chartering these towns is a hell of a job, I would know from my bigger African map published 3 years earlier, but it is much hardier to charter when you have no towns to depict at all. The inner mainland of Iceland mainly contains gletsjers, wastelands and natural parks.
Coming to a conclusion, I don't think you should keep this map this huge. I would rather suggest to merge territories together and make a more efficient smaller map of about 500-800 territories and not to make one of around 1000+ and more divisions. The size you're currently using (I guess it's the maximum) for your Icelandic map is preserved only for the most biggest maps on the site. I don't think you should blow your map out of proportion like that.
Another advice coming from your Belgian friend would be to make the gletsjers impassable. [NL] Lucas once did this before with this gigantic Europe map and I thought it would be amazing if you could do this too. Impassable lands would make the map more interesting and give the map an artistic impression. Screenshot from [NL] Lucas Europe map:
This creative input also doesn't make you worry about naming stuff using a random generator. Iceland's geographic composition is quite unique and it should be shown.
Last but not least, your borders overlap. This probably has to do with you drawing all shapes by yourself and not using any other tool rather than the pencil tool. Drawing all the shapes by yourself takes way more time and effort I could say. But if you're using Inkscape this should work out to fix the problem.
1. Draw a bigger object that encompasses both territories (in this case the whole island of Iceland)
2. Select the pencil, and draw a line where the border should be (the border of that territory)
3. Select both the line and the big object
4. Click Path -> Division
and voilà you have a clean border!
note: for bonus borders we use a different method that involves CTRL+ALT+K but that's for later. Since you don't use bonus borders in your map, this should work out fine. Additionally in this example I used the bezier drawing tool for drawing stuff which draws straight lines instead of curved lines and works way faster than the pencil tool. Perhaps you could give that a try as well?
I'm glad I could help.
Edited 12/24/2016 11:45:53