Personally mine is planned. I set a budget and then look real hard at what I am comfortable with if I excide that figure. I bought used but I was shopping new at first. $90K for the Max seemed ridiculous to me. So I used the website like everyone else and built the Max I wanted, all options. I wasn't at 90K but close, and tax and prep, etc. I was still under but much closer to the dealer's numbers. Having a base of 62K I figured I could get used for that number, and I was very wrong if i wanted a 1yr old boat. But that is how I set my used budget moving forward. I ended up finding a Mojo at that price and before scheduling the in-person meeting came to the reality that I was being scammed. I then found my 2015 for less that my budget and it has allowed me to add extras and clean up things and still keep my accounts tight.

Back to the new purchase, I look at it long term. Am I ever going to pay this thing off and keep it 15+ years or is it basically a long term rental? If it is a rental resale and options are going to win out. The extra 15K is never going to hit your pocket, but the next buyer will want the 15K in options and make it easier to sell. You are going to pay $2 more a month on your "rental" then someone else is going to assume your "rental" and then they will pay the remainder.
But why not jump to the luxury version? This again comes down to monthly payment. Buying a 90k boat and paying 675 a month or buying a 104K boat and paying 677 a month, no one cares. Jumping to a 160k+ boat is now getting into $1000 month payments and hard to swallow (House vs Car payment ideas). Also, it is harder to find the next buyer knowing you still need a large sum of money to get away from this long term rental. Most luxury vehicles have higher depreciation and the first owner takes to larger bite.

Just my $0.02, but it works in my head. I want the luxury of a top tier boat someday, but the smaller payments are much easier to make when the white stuff is falling. The goal is to break even (or make a buck in this economy), but I shall see in the coming years.