Nick,
Thanks for the pics.. It is clear that you have two inputs to your pump, the Skimmer and the Main Drain. As I said before, your main drain will not really have enough suction to suck up dirt. If you brush dirt into a cloud over the main drain, a little will get into the main drain, but not enough to make it worthwhile.
I suggest that you close the valve to the main drain so that it is only open about 10% and leave the skimmer open at 100%.. This is the best setting for most pools. To clean the bottom of the pool you need to vacuum the dirt up, just like you do with a carpet in your house.. You can do this three ways..
1. With a manual vacuum and hose
2. With a suction side pool cleaner
3. With a Robot..
I use low voltage Robots to clean my pools and love them..
Thanks,
Jim R.