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Upgrading from S60 to 70D, trading in multiple cars?

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It really shouldn't be a problem. Tesla doesn't process trades themselves. They partner and have the partner take in the trade for processing without regard to your purchase. The only "benefit" is they carry the numbers over to the purchase of the new car, so you get any tax benefit and don't need to carry the cost of your old car while the funds clear. My dashboard let me input the car I wanted to trade. I then got an emailed quote for the trade in. No reason you couldn't then update the info and get a new quote and have your DS use both when preparing the final paperwork.

As a side note, I've had friends do multi-vehicle trade-ins with other makes. Never was a problem for them.
 
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I too traded two cars ( a Leaf and an Infiniti) for our 2nd Tesla- an inventory 85. (which by the way we got a great price on!) We did this at the end of March and Tesla handled the whole transaction- They got rid of Automation as a partner sometime in the last few months. They do this all in house now. Be prepared to get 30% less than retail for your trade- which is about right since the seller ( which won't be Tesla unless you are trading in another Tesla...) has to make a profit, and Tesla will just wholesale the cars- Both of my trades are now for sale in different parts of the country for almost exactly 30% more than I accepted in Trade. I know it's hard to swallow, but that is business. If you don't want to mess with people coming to your house, or advertising, this service is wonderful. And don't forget in most places the trade in value offsets the sales tax. Tesla made it very painless and had our trade appraisals finished in 24 hours and completed the inspections about a week later, They picked one of the cars up at our house and we dropped the other one off when we picked up our 85.. I was very pleased.
 
I too traded two cars ( a Leaf and an Infiniti) for our 2nd Tesla- an inventory 85. (which by the way we got a great price on!) We did this at the end of March and Tesla handled the whole transaction- They got rid of Automation as a partner sometime in the last few months. They do this all in house now. Be prepared to get 30% less than retail for your trade- which is about right since the seller ( which won't be Tesla unless you are trading in another Tesla...) has to make a profit, and Tesla will just wholesale the cars- Both of my trades are now for sale in different parts of the country for almost exactly 30% more than I accepted in Trade. I know it's hard to swallow, but that is business. If you don't want to mess with people coming to your house, or advertising, this service is wonderful. And don't forget in most places the trade in value offsets the sales tax. Tesla made it very painless and had our trade appraisals finished in 24 hours and completed the inspections about a week later, They picked one of the cars up at our house and we dropped the other one off when we picked up our 85.. I was very pleased.

Go out and get estimates elsewhere before taking 30% less. Tesla offered me $18,500 for my trade-in. I went to a dealer and CarMax and had 2 offers of $22,000 within an hour. Even with tax savings of 7% on trading in, I came out $2200 ahead.