Hi Jeff,
The first step to get this fast established would be:
First get the terrain, perhaps a tiny little bit larger than needed.
Then use the Splines to get a flat shape that has already the “cut” inside. Outside spline, then cut spline, placed into a loft. One Cap is disabled!
The Loft [NURBS] will allow for adjustments of the mesh density, for the main part and the cap. Do this carefully!
Use the Connect Object, to connect Main part of the Loft and cap, otherwise the cap will be projected as the main part of the Loft.
Place this under a Null and use a Surface Deformer. The Surface Deformer needs to be initialized and then set to UV Projection.
IF that works to your liking, use the CSTO (Current State to Object) function in the Object Manager>Objects.
You get for the cap a single Selection Tag, double click it to activate the polygons. (The rest of the scene should be set to invisible for now)
Use the M~T (Extrude) option, and extrude -0.01 or less, just to get a new edge.
With the selection active, use the Move Tool and move the selection down in P.Y. to get your “flat sink hole”.
I guess the mesh looks better—if done carefully—than the Boole. At least you have a lot of options to adjust the mesh prior to that.
I have attached the scene file. As usual I do these things each time newly, to see if it works as before. A scene file is a clear feedback.
BTW, a projected Spline on a standard Landscape-mesh works great as Knife-Guide.
All the best
Sassi
P.S.: Perhaps I said that before, but the Spline as Knife is something people like to have, there more people suggest this to MAXON, the better.