This is my first winter with the Chubby. I find that poking is the best method to get the ash to the pan.
First, I look at height of the coals in the burn pot. Next, shake 3or 4 seconds. Next, look at pan. If by some miracle, it is full, and bottom of grate glows red, I'm done. I believe this has happened once, but I can't remember when. Usually, I poke from under the grate until I see a red glow, and shake again for 5 seconds. Lastly, I look to see if the coals have dropped in the burn pot. If not, I poke around the edge of coals from the top, until they drop.(bridging) Add one scoop of coal, open ash door, and let it rip for 5 minutes before filling the pot. I've never had any clinkers, but the ash build-up on the grate is the only downfall I see with this method. I run the Chubby at 300-350*, using Reading anthracite nut.
Sorry about being long-winded on this. Short verse: Find what works for your set-up, and keep warm!