Been back into simming a bit. That leads to trolling old threads....
Seeing how you revived this thread after three years, I figured one year later an answer might still be welcomed.
My process is convoluted... a bit... but it's how I did it all the time. Sorry for being too thorough, but I just don't know how often you mess about with such things, so I wanted to be, well, thorough.
First, level the majority of the terrain in the area you are working at the base height you want.
Second, about five or so squares away, draw a straight section of wall for about 3-5 squares or so.
Next, grab the square terrain raising tool; the big version so it raises a larger area at once. About a square or so away from the wall you just made, raise the terrain up to near the height of the wall.
Now go up a level to the second story, so that you will see the little highlighted squares coming off the top of the wall. Grab the flooring tool and place one square of flooring on top of the wall near your raised terrain.
What are we at, step five? Anyway, grab your stairs tool, one step wide. Now draw a single section (four actual steps) of stairs down to the raised terrain so that the fourth step down reaches the ground. The game should level this square at the bottom of the stairs. We have now raised the terrain exactly three sections of stairs up from your base height. You can delete the stairs and the wall now if you want.
Next, grab the terrain leveling tool and use that square you made at the bottom of the stairs and drag out a 5x5 or so section of elevated terrain.
Back to the stair tool. On the elevated ground, drag down one section of stair. Now we are two standard stair sections higher than base. Do this one more time so that you are now one standard stair section taller with your terrain.
Delete all your stairs and level this new height over your 5x5 section of land.
9. I really need to number this step... and the next several. On the edge of this heightened area, draw a wall at one edge of the raised area. Two squares away from this wall, on your original land level, draw a parallel section of wall.
10. Now grab the terrain softening tool. The smallest sized circle always worked best for me at this step. Put it on the grid line on the terrain between your two walls. Hold down your mouse button to soften the points of the grid between the two walls. The game should pull this terrain up to make an angle between the two wall heights. Keep holding down the mouse button and moving it along the grid line between your wall sections until at least two points next to each other on the grid line don't move up or down any more at all, no matter how long you hold the mouse button. This new line of terrain is two steps taller than your base height. Smile to yourself. You are very nearly there.
11. Delete the wall on the top section of land.
12. Get that wall tool again. On one of those two points that would not move up or down anymore, click to start your wall, but drag it diagonally across one square in the direction of the raised land. The game will give you a flat square at this new height.
Delete the diagonal wall and terrain level your raised land to this new level.
Repeat steps 9 - 12.
That square of terrain you just leveled is now one step (you called it a click from TS2 days) above your original height. Do with it what you will, make it do your bidding, etc, etc.... Reading out the steps like this seems as if it will take forever to accomplish in-game, but it really doesn't. Maybe takes 30 seconds to a minute at most to get any level of height you want once you get the hang of it.