It's my opinion that.*A well cared for used boat can be every bit as good or better than a new one. You are not looking at a car that depreciates by road milage. A good hull especially fiberglass and a good engine. What else is there that is really needed .You put a boat thru a refit and you have a new boat. As long as she doesn't leak top and bottom. You're good to go. If you don't love to work on your boat. Buy a new bleach bottle every couple of years and take your depreciation.
I wouldn't even think of buying a new boat.*
If you plan on cruising you need to know every system on your boat and how to effect repair.
So if you didn't install or repair one of those systems how can you fix it? Boat ownership is way more than just buying a boat putting fuel and oil in it. Paying you slip fees and going. Why eles would the number one name for a boat in the U.S. be [spoiler]Obsession.
In the end it comes down to what do you want a boat for?*
As someone else said "It is not the voyage It's the vessel." or was it vise versa?