My other thought was to create my own custom "toolip" using
NativeWindow when a user hovers over the systray (but would like to
get it to work with
possible)...any other suggestions/tips/thoughts?
I don't believe this is possible. A better strategy may be to
change the tooltip when the state of your application changes such
that the text should be updated (rather than in response to a user
event). However, I don't think the tooltip display will change
while it is already open.
Using a native window wouldn't work in this scenario, either.
The difficulty is still detecting when the mouse is hovering over
the icon. It is also not possible to definitely locate the icon on
the desktop, although you can guess using the usableBounds property
of the Screen class.