Like nearly everyone with an older used boat, upgrading is always in the back of my head.
1999 Tige 21v Wakeboard edition. She has about 650 hrs, and is immaculate. Original tower (has never given us an issue), bimini, upgraded prop, and Stargazer. Ballast is not plumbed, but otherwise, besides bells and whistles, she has everything we need. One of the biggest perks is she's paid for. Obviously, there is a lot more to it than just whether it's worth it or not, as I love not having a payment.