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Will an 8 year old Model S be almost worthless?

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True -- that's encouraging. But keeping an old car on the road is more than just having a current version of the same car on the road.

Tesla has done an admirable job of making newer iterations of parts work on the older cars; see for instance the newer battery packs or updated drive units. Other companies will make a terrible mistake in a part and just keep selling that busted (or will be busted after 2 years) part forever until everyone gives up. See also audi valve tensioner or tiptronic transmission.

Other things are important to the car that aren't in newer versions of the S; IE what happens if tesla drops availability of the 40a charger or other stuff that's exclusive to the early generation of the S platform? They're the only supplier and if they stop it isn't like Bosch or ACDelco is going to make pattern parts.

Also, availability of things like trim parts is actually important to keeping a car in good shape. Once an Audi owner lets the amazing 57 part hydraulic cup holder break and stay broken, it's probably only 2 years away from the salvage yard.

So far though, I am cautiously optimistic that they'll support these things for a reasonably long time. The MCU upgrade is a perfect example of how they're supporting "legacy" cars in a way that seems to indicate that they're not going to just abandon them.
If I’m not mistaken, the newer battery packs, 100kwh, will not work with an older non 100d model s. The replacement will be a refurbished 85/90 pack.
 
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A 2012 Signature Model S will end up being a good buy as a collectible/hobby car and will go up in value in the future but using it as a daily driver would end up being more expensive than buying or leasing a new or late model used Tesla. This true of any old luxury car but even more pronounced in the case of Tesla because they have built a moat around their new car sales by restricting the availability of diagnostic and programming software, parts, and special tools just like Apple has with their phones. This is by design and has worked well so far and won't be changing anytime soon.
Not sure I would buy a 2012 Model S today. But if you really have your heart set on it, make sure you bookmark this address.

 
I did the same. I bought a used 2013 S85 knowing that I could have a potential $20K repair a few years down the road should something catastrophic happen with the battery pack outside of the warranty. While even used, it was the most expensive car I've purchased but I needed a car that qualified for the solo-HOV access, had plenty of funds in reserve, and it would be nice for my wife to be able to drive 110 miles to work and back without needing to charge at the office. We also have a 2013 Fiat 500e that she used as commuter car but the HOV decal expired and range was limited such that she HAD to charge at the office among some 50+ other EV drivers.

I bought the car hoping that 3rd party support would have grown faster as Tesla employee turnover remained high, and I was hoping that the grow adoption of Tesla vehicles would drive the parts and service costs down. Neither seems to be playing out in a significant way. I would love for our 103K mile old car to be more sustainable I would happily pay $20K for an upgraded battery if I could get some assurances that the replacement pack would last another 4yr/125K miles. However, I'm prepared to part the car should some catastrophic failure present with no upgradeable battery option with warranty.

I wouldn't recommend or not recommend an older Model S, but I would strongly consider a used BMW i3 with the medium or larger battery pack for your commute. Having a small EV is great in a metro area or crowded tourist town...parking, maneuvering, and navigating through traffic is much easier than in the Model S. I'd say the S shines on intermediate to long trips; the long wheelbase, aerodynamic shape, and driver sight-line makes the car a pleasure to drive with minimal fatigue.

If I’m not mistaken, the newer battery packs, 100kwh, will not work with an older non 100d model s. The replacement will be a refurbished 85/90 pack.

They've made a version of the 100kwh pack for older cars using 14 instead of 16 modules. If you're getting a warranty replacement HV pack you'll maybe get a refurbished older pack or maybe get one of these (or maybe even a refurbished 100 missing a couple modules). If you buy a new pack, you'll get one of these 350v 14 module packs, presumably with fresh modules. See also

If we're talking about "life with a car after the warranty's run out" ... almost any traditional ICE manufacturer seems like an even worse bet given that all "old" EVs (i3 / egolf / fiat 500e / etc) are weird compliance cars or science experiments. They're not halo cars or core to the success of the vendor or dealership, so you're likely to not see the best the vendor has to offer.

A leaf or a bolt/volt is a known quantity and enough were made that some dealerships will probably know their way around them without waiting for the EV certified tech to fly in from corporate (if they'll see you at all for an EV specific issue). But again, I doubt you'll be seeing a vendor's best support with these vs their "mainstream" offerings.

My wife has a 2013 hybrid Q5 and a fan assembly in the hybrid battery went wonky; it took them 5 weeks to get a part which I suspect they actually had to make not find. I don't expect these parts to be available for nearly as long as the "normal" q5 parts.
 
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