There is a problem that the SketchUp team could fix. The tool tip is intended to appear a fixed distance away from the cursor, but it decides where that location is at the time that you invoke it. Some amount of time later the tool tip is ready to appear, and it appears at the cursor relative location it stored a little while ago. I’m only talking fractions of a second, but it is very easy to mouse over a handle to trigger the tool tip, and have moved the cursor a few more pixels before the tool tip appears.
If you’re doing that movement from the top left, mousing down and right, it it possible to get the tool tip to appear under the cursor. On Mac that just has the effect of making the tool tip disappear, you briefly see it flash on and off.
So, the SketchUp team could make a tiny change. Instead of:
detect rollover, note cursor location, create tool tip, show tool tip relative to the stored cursor location
detect rollover, create tool tip, now look at where the cursor is, and show the tool tip in the correct place.