What you will loose is perhaps international characters. Unless of course care is taken to convert from Emacs representation to whatever w32 uses (UTF8?).
I think that has been done with menu strings (which is probably what I confused this with) on several platforms already, and it might also be possible for tooltips. However, I don't know how hard such a conversion would turn out, and I don't know whether there exist any serious applications that indeed require the interpretation of text properties for tooltips.
The same procedure as for menu strings should work OK (well, at least as OK as for menus).
Jan D.
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