I have two of the rakes you're talking about. They're wide rakes for grading dirt and such. I might try it out next clean up.
Thing is, for me, I bag them up with the mower. I ride around on the mower looking dumb for the first 15-20 minutes backing over the lawn in a random patten to bust up the leaves some. Then I start to bag them. I found that if I back over them, it doesn't really bag them that much until you move forward. It just windrows them in a pile. Makes it easy to get more in the bags.
Corey, I asked about the time frame to contain all the leaves you were blowing around into a pile because I did a clean up a couple weeks ago about that same size. It took me just over 2hrs start to finish but I had them already loaded so I wouldn't need to come back. Plus you had someone helping you.
I'm on the fence as to whether or not bagging them as you go versus blowing them into a pile and then loading them. I think it's a wash to be honest.