Andy, this is great info. I am quite surprised that the team race guys haven't tried it or stumbled upon it. It might just be so far outside the box that nobody ever thought it would work. I think the starting issues might be a problem for team race where I believe there are points awarded for being the first in the air.
What about a venturi fitting that goes over the carb and has a small tank for starting fluid? A quick spray into the tank, slip it over the carb and apply the starter. Maybe a temporary filter type of device that you would soak in starting fluid and remove after it starts? For larger engines it might be best to have a small tank of starting fuel with a valve to switch to the main tank after things warm up. I think this could be done with the fueler valves but plumbed such that the engine draws fuel from outside the model until the hose is removed. Fueler valves usually cut the engine out of the loop while you have the fill line plugged in. Instead of doing as the instructions say, connect the tank line to the carb so that the engine draws fuel from the fill line outside the model when plugged in.
Head temperatures of diesels are lower than glow engines so I don't think overheating will be an issue. The temperature of the engine does have an effect on the compression setting needed though. Some of the heat of compression when the engine is cold is lost to the cylinder and head. This is why you need to increase compression to start many engines. The smaller the engine, the more of a problem this is. As the engine gets smaller the ratio of surface area to volume increases such that more heat of compression is lost to the engine components. This is also why smaller enignes need more oil in the fuel and less cooling fin area. There have been 1/2A glow CL race engines without fins at all. Once one of our diesels is up to temp the loss of compression heat is small and compression ratio is adjusted accordingly. Over cooled engines will have problems when idling and have trouble with transition. This is a complicated matter and I haven't gotten very far with my research ont his topic. It's something I'm trying to learn about in my four stroke conversions to prevent excessive change in compression ratio requirements at different throttle settings and resulting temperatures.
Lastly, some interesting reading.
http://www.freepatentsonline.com/2583499.pdf
Greg