Hmm look into a 16tile auto-tiling, as this is based on that kind of thing. You got your edges, the corners, inner corners, and then double corners. It's hard to explain it in text. But if you've used game maker studio, it has an option for 16 tile auto-tiling inbuilt. So maybe you can look at some tutorials for that, it should give you the right ideas or help you understand it maybe.
For the cliffs however you will have to do some custom stuff, as there is no good standartization for that kinda thing.