As a rookie diesel owner and recent diesel boat shopper I completely understand your apprehension.
There are no guarantees in life, but with the right amount of research about the idiosyncrasies of the particular diesel motors you're looking at, and a proper pre purchase inspection and survey of them you increase the odds of getting some good motors in a great boat.
I'm still kind of afraid of diesels because of my absolute lack of experience with them, but I have to say that I absolutely love having them in my boat.
My friend had some grief with the Cummins in his boat, but once repaired, the boat performs amazingly.
I'm super jealous of the room he has in the bilge of his 05 420 DA. The mechanic did the job standing up like a gentleman, and was able to stand and walk around the motors to check things and record numbers throughout the test ride.
He and my friend were smart enough to plug their ears, I wasn't. Those things are loud as heck at WOT, and cruising speed ain't much better.