I have found that some of my most fun games have been on generated maps, as it forces you to think creatively about how to win without having some practiced routine and build order that suits the map. Some of the really mass/reclaim rich maps have been the most exciting and varied.
Unfortunately the map generator seems to have been removed from the 1v1 ladder rotation.
It would be a lot of fun if there was a 1v1 ladder mode that solely plays on generated maps. Perhaps there could be two or three different sizes?
What do you think?