That is the best RMH drawing I've ever seen. I love it!
I have a masonry chimney as well. Oddmar, I think your explanation is correct and does a good job of explaining why my stove can be trouble if I let everything cool off. However, there's a flip side to that. Once you warm that masonry chimney, it starts working for your draft. I can start up after a weekend away and the thing pulls like crazy, you actually can feel the draft when you hold your hand over the feed before lighting the stove. The trick is to get it pulling at first so you can get the heat into that masonry chimney. I use a candle in my wall thimble for a while before I light the heater in the fall, and try to do my first start in the right conditions. After a warm day, so the house is fairly warm, but on a night when the air has cooled quickly. After that though, as long as I burn once every third day or so, I'm good.
My neighbor's RMH has a fairly long vertical section of uninsulated pipe, and he spends a lot of time away from home so often does cold starts. He has to be really careful or he can easily create a "smoke plug" like you describe. I am keeping my eyes open for cheap used insulated flue pipe for him, but man, that stuff is crazy expensive. I found some at a salvage place and they still wanted $18/ft or some such.