To stick with 2nd gen or make the change??

"Yaaa... no thanks" is my usual answer. I get the dealer "offer" every couple months. Latest was 15k for my 06 w/240k miles on it. He only calls when he has nothing worthwhile on the lot. I drive by it every day haha.

 

Hopefully there was a tube of personal lube included in the offer?

As an example of this shill being common, I've been getting those letters, in some form, regularly since 2004, which is when we bought the Highlander. Even though the clearcoat is now failing and it has 111k, they still 'need' it.

From a financial perspective, pay off what you have as fast as you can. Continue making 'payments' to yourself, saving up enough that your next purchase can be cash. You'll enjoy it a lot more when it's all yours.