Baloon Tooltip with Close button

Please see my response to what appears to be the same question you have here:[^].

But, the idea of having more than one ToolTip open at a time really means you are no longer really using the "classic" model of a what the WinForms ToolTip "is:" which is one, and one-only, instance open at a time ... no matter how many ToolTip controls you put on your Form, no matter you set the 'ShowAlways property to 'true.

So, imho, you are asking for a solution here that does not allow using the WinForms ToolTip Control, but will require you to create your own special Form, or UserControl, class, and instantiate multiple copies of it, implementing all the logic necessary (including use of Timers ?) that you require.