Windows and Hints in Delphi
First, what version of Delphi do you use?
Second, I recommend you try creating a simple application from scratch, with just one form and say a tool-button (or any other control that can show hints), with ShowHints activated, and see if it shows. If on such a very simple app you'll get no hints, I would recommend reinstalling Delphi, maybe something in your installation is screwed up...
I bet you're on XP and your installation is rather old.
A friend of mine had this exact problem in his machine. No VCL hints were showing up in his machine. That includes the apps he built, the Delphi IDE he used (7 afaicr) and any other Delphi built app he had on his machine. So we had concluded by blaming his WinXP instance which has been on the run for the last 2 years with a lot of garbage in it (most likely it was some app he installed sometime that was hooking messages at some point causing this weird behaviour). It might be your case as well.
ps. Another interesting point - the hints were showing up if you set Application.HintPause to a low value like 100-200. You may want to try that as well.