I do realize all of those errors, and they actually weren't to improve gameplay, they were a result of the techniques I used to draw the landscape, although I do agree it may help a bit on a live game.
To hep you visualize the problem, here is the map I drew the mountains from:http://img3.wikia.nocookie.net/__cb20100419123101/lotr/images/1/12/Map_of_Beleriand.jpg
I overlayed it with this map, which is what I drew over:http://www.elvenesse.net/maps/Beleriand_complete_Map.jpg
Now, after I matched up the coastlines, I found that the insides of the maps didn't match up directly, So I used Gondolin as a central point to Match up the mountains with their respective locations on the Atlas of middle earth map.
This worked well for the majority of the map, the only real problem was that there was a huge amount of territories behind the Ered Luin, which isn't really too big of an issue.
However, the Issue I found was that There wasn't a really good way to represent the pass between the Ered wethrin and the Echoriath, since it's pretty tiny and it has to have this HUGE circle in the middle of it. So I decided to just move the Entire Mountains that Surrounded hithlum in a bit, to make the only thing between Echriath and Ered Wethrin The river Sirion and Minas Tirith.
This in turn created the issue, but Solved a pretty major issue I was having, Albeit making the geography a bit Off.
I'll look into creating some kind of sea links.