In landscape painting mode, the target circle doesn't always line up with the crosshair. Sometimes they're offset by as much as a half-screen. Why is that happening and how can I fix it?

at least to my understanding. UE4 scales the Rendering to the Render windows, perhaps Your screen is too small Try full screen “F11”? also Check for duplicate Landscapes. There are also two Slider values for one for Fallout and one for True, make sure those are pretty tight. another possibility is the Paint tool paints by Vertex in the Editor if your Landscape Geometry is too large
Painting it would be an Eyesore causing the painting to be off.