You only live once....as far as we know, and if we do have another life you may not be into boats and surfing in the next one so you better just enjoy this one for all it is worth. My Dad died of Cancer pretty recently, when we found out he wasn't going to be with us much longer my sister said to him "Dad it's time for the bucket list" he responded " I don't have a bucket list I've done everything I ever wanted to do" and he meant it. True definition of success in my mind.
If your finances can handle it and it doesn't put your family into a vulnerable spot, if boating and surfing is a passion...man take the upgrade and don't look back.