<prompt> Human: As the title says. Have a 2011 Toyota Tundra that is paid off. Still in great condition, and under 40k miles. As of today, I could get 24-27k in trade in value per KBB. My payment was previously 520 per month which we are now calling our vacation fund. I know that this sub normally advocates keeping after paid off and saving the money that normally went towards the payment, but in this case - am I better trying to trade it in or sell it when it is at peak value? Looking to buy another new truck, probably in the 40-45k range, so it would obviously take a big chunk out of the amount I would have to finance for new. My credit is such that i would be financing new at the lowest possible rate - 0-2 depending.My worry is that the value is going to start dropping pretty significantly for my current truck in the next couple of years  <response>: Do you really want to have this luxury?It seems like you are trying to owe another 20k for little to no actual gain. I think the awesomeness will wear off before the 2nd payment of 500 and then you will just owe another 19k for nothing. 