How do I get from A to B? (Photo Example)

Question

I'm currently working on making my Game of Thrones Risk Board Map. I've got to clean it up quite a bit before it's done, though. I'm not quite sure how I would do the following:
Make the smooth black lines used for the internal borders
Thicken the already existing land-ocean border lines
Add the inner "highlight" that goes along the region (blue/red) border lines
Color the inner portion of the land a certain color
Seamlessly remove landmarks (such as islands and labels)
Add the travel routes (dotted lines)
I've attached a picture detailing what I'm starting with (A) and where I want to be (B). Any help is greatly appreciated! I know I could likely search for the individual fixes, but for whatever reason, I'm horrible with nouns and distrusting in the fixes that I have found. Thanks again.

Answer 1

Sounds like you already know what to do, it is just doing it. I don't mean to be sarcastic, but it really is that simple for majority of your issues.
Use the pen tool and outline each border. This path or I should say shape can have as thick of a stroke as you like, any color and can have a fill.
The issues that would be a bit harder is removal of the islands and text.
For the islands it may be easier for you to just give the ocean a new fill then that fill can overlay the islands which would hide them and all text on the ocean.
As for the land, the pen tool took care of all text and mountains when you used a fill. If you would prefer to keep the mountains, you could set the layers blend mode for each shape for the land, then would tint the land with color but allow the mountains and text to show through. All that is left is to use the rectangle shape tool or pen tool to create a shape just around the text and give it a fill that matches the lands fill.
Now you can use the text to to add your own labels.
I hope this helps, and again i din not mean to sound sarcastic, so my apologies for that.