Well....if you listen to the response of this board...they're going to say you NEED a bigger truck then a gen II Tundra. They are going to think you need a 3/4 ton diesel.

You're going to be pushing the absolute max of a gen 1 Tundra. I think you would be better off trying to find a Ford F150 from that era. They're bigger, stronger trucks and would be a better tow choice for your boat.

I still have at least 3 more years to go before even thinking of replacing this truck. Maybe even more as it is probably at less than ½ of its design life. So that would make six years or more w/o a payment. Am I bored with it? No way and I'm not so sure about these new-fangled partical trap systems either.

There's no reason to haggle. Test drive what you like on the front line and then later ask for your best price on the exact vehicle you want with all the options you desire from several different dealer's fleet departements over the phone. Go with the one with the best price and be done with it.

If you have a trade, sell it private party and skip the dealer's profit on that.

Obtain your financing from the best time value of money offered by your C.U., bank or even the dealer.
Buying a car is two separate transactions if you have no trade; best price and best cost of financing. If you have a trade, it is three separate transactions; adding in selling your current vehicle at the best posible price which most likely will not be as a trade-in at the dealership.

The key though is to keep your vehicle well beyond the payments.