Hello Mel! Now we know what you are thinking. I feel a little disloyal to my Investigator 563, however I have lusted after a Top Hat ever since I had her baby sister, the Bluebird 22.
Anyway, back to your topic. Have you read
viewtopic.php?f=3&t=951&p=5335&hilit=diesel#p5335It is not that outboards have superseded diesel inboards, it is just that inboards are more expensive initially, and it would be uneconomical to fit an inboard to a current boat that does not have one. Diesel advantages are less fumes, lower noise, can plug on forever. So if you were doing long offshore trips, having a diesel would be good.
An outboard in a well, IMHO, based on my experience with the Bluebird and the Investigator, is that a well mount is far superior. There are no problems with cavitation, and you can easily get to the motor to de-bug if it starts to play up. CF with an OB on a transom bracket, once on the Investigator cavitation in choppy confused seas caused the shear pin on the propellor to fail, and there was no way I could get to it to fix it at sea. In a well it would have been a breeze to pull out.
WRT thrust, the key issue is the correct choice of propeller. For the same HP rating, the thrust will be the same, diesel or outboard. From what I read here, outboard power is limited by what will fit in the well, but I guess 6 to 8 HP should be enough.