Thanks troop. I am seeing KBB fair as $16,825, what am I doing wrong-is KBB on the web different?

My inkling is that the web pricing services are inflated compared to the pricing services that the dealers subscribe to in order to keep prices high.

I had a Used car manager hit an Escalade the other day at $10,000 below Fair condition. We made the deal, took the Escalade to the SD Auto Auction, and NO ONE put a single bid on it.

ANything with 8 cylinders right now you should be able to buy retail for wholesale Blue Book or less.

FYI two weeks ago I bought a 2004 Toy 4 runner V8 Limited for 2/3 of the KBB #.

I think with a Gen I Tundra you will be pushing it with the boat. I know first hand we had a 2001 and 2002 Sequoia the would struggle with our Rinker 232 Cuddy. But the 2004 Tundra did a great job with it. The differecne was in the rearend gearing.

When we got the Ebbtide 2600 I only towed it 2 or 3 times with the tundra and it was not fun.

The QX56 did much better towing both boats.

As you know the Duramax towed the Rinker like nothing and almost got a ticket. With the Ebbtide you could tell it was there. If you want to stay 1/2 gas I would look around for a Chevy or GMC with the 6.0 liter Tow Max package.

I have had the experience owning both a gen 1 and a gen 2 Tundra. My boat is around 6500 and 7000# so I am in a similar situation to you. I will tell you that with that weight the gen 1 can do it, but your will definitely feel it and you will be pushing things a little. The longest tow I did with my gen 1 was about 80 miles and the truck did fine, but it was working.
My 2007 pulls the boat like nothing. The truck is just built for heavier loads and it feels so much more comfortable. The 5.7 pulls like a champ.
In my opinion I would go for more truck than a gen 1 to pull your load. If you had a smaller boat, I would consider the gen 1.

The 1st generation Tundras and the T100's tend to chew up ring and pinions when towing 5000 pounds or more over the long haul. Fine for occasional towing though. The new Tundras have the beefy 10.5 or 9.5 ring gears which will take anything you put behind it. Toyota realized this in the second generation.