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Car Shopping Advice, Purchasing Tips

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I didn't mind the engines in all the ICEs I test drove. I really liked the sound some of them made. Couldn't stand the transmissions though. I came from a manual and found the behavior of the automatics to be infuriating. They're always shifting, and so before you can do anything you've gotta wait a second or two for it to change two or three gears.

The only thing I really thought I would have run away with was the headsup display - wow!! The speed/direction/speed-limit is projected into some distance in front of you and passengers/others cannot see anything. That was amazing.
When I test drove a 5-series I found the HUD to be incredibly annoying. I was trying to figure out how to turn it off after 30 seconds. I have no need to see my speed right in front of everything, it just gets in the way.

Totally agree about the rest of your observations on the 5-series. BMW has completely wrecked that car.
 
My wife took delivery of her MS 75D in Dec. Her previous car was a 2004 Infiniti G35X, which was a truly excellent car and went strong for over 13 years! So, to give Infiniti a chance, we test drove a Q50 Red Sport (400 hp) a few days after we took a 24 hr test drive of the Model S. The Red Sport was a great car, but the salesman took one look at my wife and just said, "You look underwhelmed." He was exactly right. A month later she ordered her Model S. It is such a joy to drive. (I am hoping to get 2-3 years out of my Acura, at which point I am also going to seriously look at the S).
 
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Since you sound relatively young and say you are not really experienced with many cars, I agree with the advice to avoid the Performance cars, if only because you will pay so much more that you might resent it if the car does not work out for you. The P models go through tires faster, as well, and are more likely to have the larger wheel size (21 inch vs. 19) that are less efficient, wear out tires faster, and seem more likely to fail in potholes. The smaller (19") wheels will give you more range and less maintenance headaches. (Of course you can always switch wheels and tires if you find the otherwise perfect car that has 21 inch wheels.) I also worry that previous owners of Performance cars may have worked them quite hard do they may be more of a maintenance problem than a non-P car at the same mileage. (Then again, folks do find the performance addictive!)

How far are you from a Tesla service center? That might be a factor, too, especially if you are looking for a CPO car. Nothing is perfect. Stuff breaks now and then.

As for comparable cars, that is a tough call. The Model S is not as luxurious as other cars at the same price point such as the Mercedes and BMWs that folk have mentioned. I would say my Mercedes E class was more comfortable in certain ways, and was less expensive. But the EV experience is so entirely different that making a direct comparison is difficult. For me, I was more than happy to give up a few creature comforts to get the Tesla experience. And as it happened, my spouse far prefers the clean, simple uncluttered interior of the Model S. She also loved to drive it once she tried it on the highway. She is intimidated by the car's size in parking lots, but truly loves it on the road. I have no problem getting her to share the driving on trips!
 
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Thanks to everyone above for your thoughts and advice! I did a second test drive of a Model S on Tuesday, after driving some Audis, Acuras, even a Toyota Camry (which honestly wasn't bad). None of the ICE cars had anything really comparable.

When my wife gave me the "will you be happy with any other car" line, I put my order in yesterday. Only regret is that the NEW referral benefit is Free Supercharging + $500 service credit. I'm seriously considering asking them to add the credit or just cancelling and reordering!

And now the months of waiting begins....I've already read everything on the Tesla website and I lurk around these forums WAY too much.