@Kurt91- That sounds like a lot more work than I'm willing to go through for the end result that I wish to achieve.
I think I like these areas without an overhead layer better than the ones which retain it.
I love this idea a lot. However, you have a perspective problem. If you look at the top wooden planks, they have the same perspective as the ones facing down. It gives it the impression that it's literally just straight up, like a column almost.
This is best what I could describe as your solution would be. Put this tile against the original mountain tiles and you'll see what I mean. However, your solution would be even more simple. Just cut off the half circles on the top of the plans, and replace it with a straight line, unless something else works. When it's fixed you'll see what I mean!