Larry, It is an interesting problem. I guess my age and a certain lack of alacrity is showing as I wasn't thinking about a lot of moving air. This is not a problem with the problem or its statement, it is apparently a problem with my visualization. This is how we so easily diverge in our conceptualization of initial coditions.
In still air I think there would be no contest. With moving air it gets more interesting and complicated but I'm not convinced that the small reduction in mass due to expanded hot water and evaporation will reduce the energy required to be removed sufficient to drop the hot-hot water down to the cold water's dropping temp faster and outrun it.
We are in agreement as to the means of cooling faster than the cold water aren't we? At some point if the hot water catches up with the cold water its reduced mass will allow it to freeze faster. The question is, will the hot water catch up with the cold water? Is its evaporative cooling and reduced mass going to make it drop in temp fast enough to make up for the cold water's head start? The answer is, It depends! It depends on RH, wind speed, exposed surface, R-value/conductivity of the icecube tray, i.e. plastic of aluminum, how thick, form factor of the cubes, and such.
When in doubt of the number of angels dancing on the head of a pin, get a loupe and count them! I wish I had a cross top freezer with icecube racks.
Now about the billiard ball problem that I somehow missed out on here when first introduced. I was curious if there were other solutions besides the one I came up with and VOILA... there is a really neat (I like it better than mine) solution. The first solution listed at the site listed below is the MUNDANE one like I came up with. The second solution is, I think, way neater!
Weighing Pool Balls - Solution
Pat