From what I've heard, those don't do anything from the user's perspective. It's when the CPU will progress people. I set mine to End of Season when I set it up but I still get the reminder every week. In the Bugs/Glitches thread, someone from EA said that that option determined when the CPU would progress.
I guess my next question is whether I'm gaining an advantage by progressing weekly then. Hopefully, it's set up so I'm doing it each week but it doesn't take effect until the End of Season (or whatever option one selects) but I'm guessing it isn't that way.