That is o differet than a cave, really. when you have your grass hill made, you would need several tiles of the GrassNoDraw to allow the head clearance of the character. so if you start at 0, and the ext tile is say, 10, ad then the next is at 20, (yes, you would really want more tiles to make a smooth transition) you would want, 2 tiles wide x 3 tiles of the GrassNoDraw, at those same altitudes. Then in game, once you have those placed, you simply put your static tiles down to walk in. Of course, there are ways to cover up the edges that might stick out of that No Draw Grass tile.. maybe use a Static grass tile at the first step.. or place some grasses, ferns, whatever around it.. (you see a couple trees on that pic osi used) and you are done
Hope that helps.
If not i could put some step by step pics together.
**edit
btw, I am looking for world builders, among other areas of map/world building. I have a very well evolved world atm, but am in need of some one to help get me motivated again. the shard is active, running with RunUO, on a powerful server devoted to the shard alone, on an ADSL line ( and will go to a mbit line if needed later).
If interested, anyone, I am considering the help
Screenshots are on my website below. thanks.