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When is best time to trade in S85 for D with AP?

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The problem is so many people today see a "good deal" as keeping the payment the same or lower. The don't even bother to calculate anything else, to see if they are getting screwed. If your idea of a good deal is a perpetual string of monthly payments, have at it.
I'm not going to delve into and debate you on your dubious calculations but please tell me how you can have a new car without extending payments?
(btw, we all don't finance)
(this is why leasing is attractive to many people)
if you do finance the car and if you want to own your car for many many years your theory makes sense, but if a person wants to get a new updated vehicle I don't see anyway around PAYING for it.
 
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When Autopilot was released, in my mind Tesla were doing some crazy good trade in deals on pre-AP cars. Probably a case where the residual values of vehicles hadn't yet caught up to the announcement.
I came to that same conclusion when I made my trade from an early '14 to a very late '15. tesla gave me what I felt was good value for my '14 and while I could have eeked out a few $K more selling privately the sales tax offset more than made up the money I didn't get for the car selling privately.
everyone's situation is different, YMMV
 
You now have 5-7 years of payments ahead. Financially, how exactly is this a good deal?

You also get a brand new car with the latest features.

I see your point, sort of. My dad actually made the same point to me trying to get me to lease my Model S rather than buy it b/c the lease had a lower monthly payment and less months of payments, and a smaller downpayment so it was a smaller outlay of cash than the financing that I did. But I also intend to drive my Model S until the wheels fall off which will put me ahead of the game financially.

back to the topic at hand... it is not like Tesla took away his car and gave him nothing. The new car is more advanced than the one he returned and only $1500 more expensive spec for spec if you don't count the $3000 difference for upgrading an 85 to a 90. Tesla usually gives terrible trade -n offers. in this case it sounds like it was less terrible than usual. They do not negotiate on the price of a new car. this is why the OP feels he is ahead of the game. and I have to agree with him.
 
Buy in December from inventory and you will get the best deal as Tesla tries to pump-up their delivery numbers for Wall Street. Plus AP 2.0 may be out at the time. I bet there is a referral program going then too. Also, you get the Federal Tax break on this year's taxes.