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Tesla trade-in

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You're right. He'll still pay sales tax on the Tesla side of things, but you're right that he won't be taxed on the sale of the vehicle. I was thinking that the person reporting the sale needed to treat it as income in some way, but probably not, since at registration time, the buyer would have to show he paid the tax, or would end up paying it then.

So yeah, if he didn't take the $16k off the price of the Tesla, he'd pay 6-7.5% on 16k, or 960-1200. If he can get $2k more at private party, then he'll make around $1k or less depending on local tax rate.

This. The math is pretty straightforward and private sale is almost always better, unless you really dislike the process of private selling and eating the "loss" is worth it to you.
 
It was an event less trade in process at Tesla. After uploading the pics, the estimate I got was around the "very good" KBB value. The tires were worn, and there were many minor scratches around my Prius from regular use. There was no mention of any inspection, or any adjustments to the trade in value. The trade in was as simple as me signing on my title, and a couple DMV papers.