Another factor that comes into play is how weak the used boat market is. Consider this:
Three years ago I paid 170k (too much in hindsight) for a 2002 330 express. I used the heck out of it, ran the engine hours up to 1700 or so and decided to sell it. Since I figured it would have to be repowered, I would have taken 140 for it.
I couldn't get 140 or any reasonable offer, so I decided to keep it and repower it and add some other things I wanted. Say when it's all said and done I spend another 50.
I now have 220 in it BUT the generator has not been replaced so say 20k more to switch over to the diesel generator.
So for 240 all in it's not new but I have 6 years warranty on new motors (250s not 350s), a bow thruster, power steering, new hoses etc. Plus the enjoyment of the last three years.
I've always thought a re-power was a losing proposition but I don't feel like I'm in that bad a shape. The delta between new and used seems to be at an all time high.