To Rake or Not to Rake

This is my somewhat leaf-less yard. 

My theory about the raking of the leaves is that:

1) I don't mind raking leaves. It's nice to be outside and the dogs are outside so it's a win-win.

2) If I wait for ALL the leaves to fall from the trees, then the leaves will be SO heavy that I will have a hard time raking them and it will take a lot longer to do it. 

3) I see raking a lot like laundry. I know when I'm starting a load that it's not going to be the only load I do, most likely, I'll have to do 5 more in that day.

4) I'm not asking him to do it so why can't he just appreciate that he doesn't have to do it and it's getting done... :) 

So, what's your theories on raking leaves? Are you a wait until all the leaves have fallen from the trees and then rake once? Or do you rake a few times over fall?