@fire-eggs and @erco77 Thanks for looking into this, I'd been distracted by other work.

I seem to have made some progress. Commenting out this line:
https://github.com/fltk/fltk/blob/6ac305a50804498b8c7ab00d23d2d4f3164b84fa/src/Fl_Tooltip.cxx#L303
seems to "fix" the issue.

I'm just testing and making educated guesses so far, but this line seems to be unnecessary at a first glance. If you look close at what happens when you enter a button - at least when another tooltip is already displayed - you'll notice that the tooltip gets displayed twice with a very short delay. To see that better, move the mouse upwards from, say, button2 to button1. And to see it even better, you can increase the hoverdelay from 0.2 to (e.g.) 0.8 seconds. Here's my working patch with test and debug statements:
tooltip.diff.txt

This is not yet a final solution, it's just a little progress I made. I'm also attaching my test program here: issue-261.cxx.txt

I'd be interested in any insights and test results. Are there any negative side effects?

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