My '02 2500 4x4 Silverado has 205,000 miles on it and I wouldn't be afraid to pull your boat anywhere. It's very rusty and not the best to look at but it runs and pulls great. If I were to sell it I probably couldn't get more than a couple thousand bucks at most. You should be able to get yourself a decent high miler in better shape than mine for less than half of your budget.
That's what I would do.
John
