I don't have any experience of
turbo engines, so I'll take your word for it that piston engines are usually more complex to operate.
In any case, my point was not that someone with 10,000 autopilot hours in 767s or whatever is going to be able to hop into a Corsair with only a brief conversion process; just that MackMeeter will probably get a better reception than a PPL with 150 hours in Cessnas. I was simply trying to encourage him ... I didn't say that he needn't bother obtaining tailwheel experience, or anything like that.
I think that five of your six points are good, but not the last one. Pushiness or arrogance will obviously be counterproductive, but anyone who "waits to be asked" will be waiting until they are too old to pass a medical examination. If MackMeeter is to have any chance of flying classic airplanes, he must quietly make his ambition known, so that he comes to mind when there is an opening. There is plenty of competition, and shrinking violets and wallflowers will get nowhere.