I found a fix for this issue.
With the affected landscape area uncheck 'Display the Components in 3D'. Cut the landscape area and paste it right back in. The area is now on the surface of the site model. Recheck 'Display the Components in 3D'.
Edit: Turns out my issue was having the landscape area go all the way to the corner of the site. If I bring it in any amount the landscape area suddenly pops down onto the site surface.
According to the documentation I have found, designer is supposed to be an all inclusive package that includes spotlight. (Please correct me if I'm wrong on this.) If this is true, how do you find the 'Event Planning' menu in designer?
Thanks.