Wide-body
The pilot is going to make his own mind up. If he screws up on landing or take-off, he is likely only to hurt himself, but it would lead to the loss of a nice aeroplane
When I was a snotty-nosed novice (last week, I think), we were told one of the worst sins was over-confidence in our ability.
I can't know how good a pilot the new owner is likely to be - he could be brilliant, and yes, the D9 is an easy plane to get to know. I'd like to know what he has been trained on and the sort of environment he was trained at - is it somewhere like WW or Enstone, or one of the bigger fields.
I wonder what sort of loading the insurance company would make, if the new owner has no tailwheel time at present.
But flying out of strips when you are a newly qualified pilot, just seems to me to be running before you can walk. I just have this image of someone who hasn't even waited to get the licence before buying an aircraft, and one where there is no chance of sitting beside another pilot - just in case.
Lots of people have converted successfully to types like this, but I'd have thought it easier and safer to go for, say a 112 or 120, than the D9.