I've actually done a number of crosses this season where I would cross the same two cultivars on the same day so that I could see how, all other things being equal (weather, time of day, etc...), how well certain pollinators perform and differences between the children plants (assuming I grow all of the seeds out. I wasn't doing it with the intention of seeing seed count differences, but that would be an awesome by-product of the experiment.
I ran into some difficulties, but I intend to retry my experiment next year when I have more blooms to work with and a little more knowledge about what works and what doesn't. (I started the somewhat unsuccessful experiment because I'm very curious to test the theory I have read multiple times that children plants tend to take after their pod parent in terms of plant characteristics.)