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Better to buy a CPO MS85 or the now discontinued MS75?

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AP2 will eventually -- some year soon -- make the S75 much more desirable and of course there is that old rule about buying the newest you can afford, even more so given the short life of the company. As for the previous comment about range, I doubt there much difference between the two given the age difference.
 
I was in the exact same position last year. I ended up getting a new 60 instead of a used 85 but prices have gone up quite a bit since then. If i was doing it today I'd probably go CPO.

Some things to think about:

1) The S85 is going to be at least 15k cheaper after tax credits. keep in mind the opportunity cost of having that money tied up in a car vs investing it. Typical stock market returns are 7%, so over 10 years that money could double.

2) AP - It's a really nice to have feature. Definitely worth the $2500 I paid for it. But I'm not sure if I'd be happy dropping $5000 for the new enhanced AP.

3) The facelift and AP2.0 didn't seem to dent resale of the classics much and the next major update of the S is likely to be a redesign of the whole car in a few years, which would impact both cars' resale values. Generally depreciation on the S has been very good. I doubt either will fall off a cliff but the 85 is closer to bottoming out. Any increases in future "new" prices would benefit both cars.

4) Frunk - the Facelift cars have the same frunk as dual motor, i.e. much smaller. So you'd be giving up a decent amount of cargo space. Now a lot of people never open the frunk, but it's a major feature of the car.

5) If you do buy new, try to find someone who's already got 4 referrals to put them over the top. There's not much point in getting a referral from someone who has no hope of selling 5 Teslas in a referral period.
 
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I was in the exact same position last year. I ended up getting a new 60 instead of a used 85 but prices have gone up quite a bit since then. If i was doing it today I'd probably go CPO.
Today, the new custom order base S75 is only $2,000 more than the cheapest past price for new S60, but you get a bunch of stuff for free, such as glass roof, power liftgate, smart air suspension, new Tesla seats, fog lights, adaptive headlights, premium lighting package (accent lights inside and outside, like door handles), and of course 1s faster 0-60. People are reporting getting sw limited 85KWh batteries with their latest S75, and a high power charger too. How much did you pay for the new 60 and what options did you get?
 
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$73k AP1 Pano Blue paint tan interior

Base was $66k and is now $69.5

Can't really do an apples to apples these days but similar spec today is about $81k

Granted that has a lot of premium features as mentioned before but at some point it gets a bit too rich for your blood but someone who was already speccing a lot more options probably has a different result. If you got a 75 with premium pack, and air suspension last year you may have spent a bit more than this year.
 
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$73k AP1 Pano Blue paint tan interior

Can't really do an apples to apples these days but similar spec today is about $81k

Granted that has a lot of premium features as mentioned before but at some point it gets a bit too rich for your blood but someone who was already speccing a lot more options probably has a different result. If you got a 75 with premium pack, and air suspension last year you may have spent a bit more than this year.
True, hard to compare base because base today has so many more features standard and a larger battery. I don't think prices went up though, they may actually have gone down a little, but the options moved around and some became standard while others got bundled like with traditional car manufacturers. If you were to compare a S75 from your era (it used to be a $9K price increase), now would be way cheaper than a year ago. Pure base to base comparison MS, you get a lot more for your money than last year.

Also you have to get Air suspension now. It's nice but I didn't want the maintenance hassle.
You have to get it but it's free now. I personally like SAS for me, but for my wife it's easier to not have to worry about remembering to raise the suspension in new parking lots, especially when parking over curbs. I get the maintenance argument and not wanting a particular option though - I feel similarly about the pano roof.
 
Many had reported getting a showroom discount after the upgrade was announced of $1000 that effectively push the S75 price to $68500 which is $2500 more than the software limit 60. Those upgrade a nice to have for those that need them, I got the 60 and the only upgrade I got was EAP.
 
Thanks so much for all your insight! I have to decide tomorrow if I'm switching my deposit from CPO to new. This is huge for me as the last car I brought was my Honda Civic in 2004. I'm usually very frugal but I'm so excited about Tesla!!