re: Questions about trading Tundra in

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This truck has been nothing but problems for the 6 years I've had it

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That's a unicorn - a lemon Toyota (and a truck, at that). I've heard tales but never seen one.

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Question is, assuming it does need a new system what are my options as far as trading it in for a new Colorado? Am I morally obligated to tell the dealer what's wrong with it? Is it a given that they will test the AC, even if it's freezing like say..tomorrow ?

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They're going to test everything. However, I would find it impossible not to at least say that the A/C has been giving you trouble. I wouldn't bother to tell them about stuff you fixed and reasonably believe to be in good working order.

But, A/C is the single most important mechanical factor for resale in Louisiana after a running engine for a used car. Believe me - they will test it. So, tell them and maybe he'll go easy on you.

You're probably better off trying to sell it to an independent mechanic shop or A/C guy who can fix it at cost and flip it versus trading it at a dealer, just in all honesty.