your thoughts- upgrading from a 1998 370 da to a 2005 455 cruisers

You're always better selling yourselves, if you can. But the prices you see are "asking" prices which aren't what the boat will sell for. They also include the broker's commissions with a little room to negotiate there as well. The top end prices are often people who have a bad note to satisfy. Those boats may sit for a very long time. I know of one 50' boat in my area that's been for sale for about 6 years. I get the feeling the guy promised his wife he'd sell the boat 'If he could get his price', but has no intention of selling. Trading in, just like trading in a car, is always the most expensive way to do it. In fact most brokers won't do it for fear of having to carry another boat. So, if they do, it'll cost you for their taking the risk. They'll usually offer to sell it on consignment, a situation I've seen abused on a few occasions. Bottom line, the less work you do, the faster you want it done and the less risk you take, the more it will cost you.

Also, if you live in a State with very high sales taxes such as IL, you don't pay tax on the amount traded in on the new boat, you only pay tax on the difference. So you save some money there.

Be careful you made one mistake when buying the first one. If you find one at a good price and a dealer will work out deal with yours and the numbers are good go for it. Looks like the one you want cost a heck of a lot a money so I can see a trade. People with high dollar boats have a hard time selling. You got to remeber if a dealer is buying yours the price will be low. But if you make a right offer on the one you buy it can work.

Be careful of dealers who will "help you sell your boat" on consignment. I had a client recently who I offered to help him sell his boat (no comission) for 30K, but he went with his marina instead. While it was there the dealer talked him into fixing an oil leak and a few other items on a boat that was asking 39K and did end up selling for 30K. Between the repair, the commission and the storage fees he walked away with 10K and a feeling of being used and abused. Personally, on a boat like yours I'd list it in Boat Trader and Craigslist and sell it myself. I also wouldn't begin looking for a new boat until I'd sold it. These day, if you miss a deal on a boat, there's another one coming around the corner.

Do you anticipate having the slip go with the current boat? I'm not sure about your area but in some high demand areas having a slip included in the boat sale is a real plus, especially if one is looking at a liveaboard situation.

Depends if you owe money on your sea ray, let say you buy the cruiser at 250,000 and you owe 25000 more on top of $50,000 your sea ray thats 275,00 plus tax. Don't rush into something that you will regret later. The good thing about trading in you do not have to pay commision on your boat and you can deduct the selling price off your sea ray on the taxes of the other boat. But that is only like $7,500 saving. If you can make the deal around $230,000 for the whole deal I say you did good. I would try selling yours for $95,000 and give that a shot.