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Best "value" Model S

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The pricing seems about right by OP... The high milage is key... Tesla only offered $49k for my fully loaded P85 at 2.5 years of age due to high milage... And an 85D is cheaper when new.
However if you wait 2 years then you will be reluctant to get autopilot 1.0 when the new autopilot hardware is just around the corner.
I'd consider getting a CPO 70D in the near future and start saving on gas soon... You do drive a lot! If you get it with financing and put your gas savings into the repayments it might not be that expensive.
 
We decided not to wait any longer when the 70D came out with autopilot. Ours only had the pano and autopilot options so it was as easy on the wallet as you could get (the CPO program was not yet up and running). I personally would not get a second tesla without autopilot but that is just me. I would also suggest not waiting 2+ years for the 'perfect' deal. Grab a test drive and then take the plunge. If you don't the only regret you will have when you finally get your car is that you didn't do it years earlier. Have fun.
 
If you keep waiting, they will get even cheaper! Seriously, you've got to pull the trigger some time. I am of the mind that with AP, the release of the Model X, the development of the Model 3, that now is a good time to "jump into" a Model S.

55 painful days left!
 
I was lucky enough to get a 2014 85S with AP. That feature is a game changer for me. I drive 100 miles every day and hold the wheel for less than 5 minutes rain or shine. While there is talk about new AP hardware in the future, hey this works just mighty fine for me. I honestly think the AP doubles the value of the car. So if you are thinking about waiting, you are missing out on driving like no one else for the next few years. As to range, I agree with previous posts. It's just about irrelevant since 99% of time you will not worry and the 1% you plan ahead and use superchargers.