Chaparral isn't exactly known for their ski and fish boats whereas Tahoe comes from a fishing heritage. As for new versus used, a used boat a couple years old with less than 20 hours on it that someone bought but realized they can't use is a far better purchase assuming they aren't underwater on it. You will be comparing far nicer models than the entry level models you mention above. I have a Chaparral bowrider and it sits so far out of the water, I am the only one who can even reach the water to even rinse my hands off and I can barely reach it. With kids, it is the most impractical boat to fish out of and so we don't really even fish. I would consider a nice fishing aluminum boat with a large outboard again nearly new for your money and not doing the combo. Just about every brand that still makes small fiberglass bowriders offers some sort of Ski and Fish boat from Four Winns down to Glastron if you are set on a glass boat. I don't know about your state but here in the second highest taxed state in the country, used boats from private parties are not taxed meaning in my egregious state doesn't tax them, maybe yours also doesn't. Dealers have to tax their used boats however brokers and private parties do not.