Ah, it's tipster... allready wondered - If you switch to "Tooltips at pointer" it should work -- I have "Use tiny tooltips" enabled also.
Me too, that's the only workaround ;)
But I've noticed another tooltip problem. I don't know if its Tipster or ItemRack.
Try hovering about the items in your CharacterFrame .. there are some slots that doesn't show any tooltips, depending on which speed you move over them.
It's not ace'd, but I think allready better then Wardrobe / Equipmanager - I just switched from Wardrobe & TrinketMenu to ItemRack. I really like it, the interface etc - since 1.4 it has the ability for Itemsets, it's still missing the auto equip (mounted, plaguelands) stuff though. I prefer to switch myself anyway...