Here is my early map concept art. I was inspired by the comments earlier on a "u" shaped hotel building. I'm leaving the actual architecture up to Doug: this is just the general shape.
View attachment 509896
The central New York Wing has a grand Atrium reaching to the top floor of the mansion, with the very center hosting a giant skylight (there could still be towers or other high points around the center, I just think a skylight would be nice in the center). The central Atrium could have a NY Steakhouse-esque Table Service, Cofee Shop, and Gift Shop. All guests enter into this wing.
The Hollywood Wing and Chicago Wings each have their own themes and are for the most part mirrored. Each have their own separate lounges with their own entries and exits, but this is only accessible to already-staying guests.
The pool could be outside in the gardens beyond the New York Wing.
Thoughts? This is all very early and can change as needed.