If this sounds like your situation then you might want to have a look at OnTop.
OnTop in Action
The exe file for the app comes in a zip file.
We decided to set Winamp to be always topmost first.
Clicking on Paint.NET brought it forward over Firefox and Microsoft Word but Winamp was still sitting on top.
Clicking on Microsoft Word next still did not affect Winamps topmost status.
Links
Download OnTop at Softpedia
