I'd expect zero issue on your grading question. The measurement would be from the bottom member to the ground, presumably on whichever side had the least clearance.
Did you get your water drainage issue cleared up? I know that if you can have your drainage pipes extend to a grassy area, you will have minimal if any issues. Maybe put some rock at the end of the drainage pipe to let the water spread out a bit then no worries. When we drain our pool down for the winter, I run it into our deck drain and out. So I have thousands of gallons going onto grass (with a few rocks first) and it's perfect, if soggy.