I'm a numbers guy, and most of the time the numbers have the biggest influence on something for me. How much did you pay for your boat? How much do you think you could sell it for? What would be the difference in price between what you think you could sell your boat for and what you'd spend on the newer boat? How much do you figure it would cost to repower your current boat? Obviously you don't need to answer or give the information asked above, but those things are definitely something to think about. If for example, you bought your boat for say $100k and have another $20k into it, but think you could only sell it for say $75k... that's a pretty decent sized loss right there, which would make me consider keeping the boat and just running it as is. That being said, if you can break even, close to it, or maybe even make some money off of selling your current boat. That would definitely make me consider upgrading to the newer one if it isn't going to cost all that much more, especially if you plan on keeping the newer one for several years and can justify those added costs. I also think buying a boat, especially a newer one, that has had a repower done to it already, or that has considerably newer motors, would be money well spent. As it seems like those that repower older hulls don't usually get the money back out of the boat when they go to resell it that they just spent on the repower, if that makes sense. I'd hate to see someone spend the "$100k" on the boat, put another "$20k" into it and then another say $50k+ on top of that for a repower, and then have their boat still only be worth oh idk... $100k? Fortunately, I bought my boat for cheap enough that I figured I could repower my boat and still make money, or at least break even off of it, if I ever needed to and/or decided to sell her. I know that's unfortunately not always the case for everyone, though.