Things start at 9pm. Unfortunately, it's the Exhibitor Reception just before, so it's a tad difficult to have our own reception... Unless I can convince the Powers That Be at Gen Con that there could be some overlap... We could say our reception starts at 8:30 (which is while the Exhibitor's Party is winding down), and then get the awards started at 9:15...
Hmmmmm. Lots of ellipses in this post.
As for the entertainment, one possibility is LukeSki doing a set, another possibility is simply having a DJ spin some tunes. Or a combination thereof.