This was supposed to be awarded back in December 2008 but was severly delayed. Bool Tools by Whaat from Sketchucation – for sale for a reasonable $10.00 on the Smustard website – adds a much, much, MUCH needed functionality to Sketchup. Anybody who has worked with SU for more than 10 minutes can attest to how sorely missed boolean modeling functions are when comparing SU to other 3D modeling software. With a simple, intuitive workflow and the fact that it just plain works and works the way you expect in most situtations – it hands-down blows away any other Sketchy contenders for the final Sketchy of 2008.
Congratulations to Whaat – keep up the good work and we look forward to your next plugin!