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Am I going to regret leaving off the air suspension option?

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Before I really even knew anything about the cars, I test drove the Model S a couple times and 100% noticed a difference everytime without being told. I love the air suspension and really wouldn't take a car without it. I'd say go for it, as I was hesitant at getting it and don't regret it one bit.

Ditto this. I've only test driven the model S, but the last few times I tested explicitly for ride quality and tire noise. I took the cars on a particulalry rough section. The first car had 21s and air. The second had 19s, and I was TOLD it had air...literally 15 seconds into the drive (over a decorative cobblestone section of road) I thought "this feels more firm than the 21s...how is that possible?". By the time we hit my rough test road I asked "Are you sure this has air?" - a quick check and sure enough it had coils. By the end of the test I had determined that the coils gave a more connected feeling with either 19s or 21s, but they rode more firmly than even the 21s with air. However, the 21s were noisier regardless of suspension. There is no free lunch. Now to be clear, the 19s with coils wer still very liveable, but the difference was enough to confirm air is a worth it for me. I don't use heated seats, navigation, or a high end stereo in a car every second I am in it, but the suspension is in play EVERY SINGLE SECOND the car is in motion...worth it.
 
I would say NO, it is not economically feasible to upgrade post delivery. Beside ride comfort and efficiency what you need to consider is road condition and driveway slope. If your driveway or places you visit has a steep slope, keep in mind that the break-over angle of MS is only 11 degrees. In those condition, air suspension will come to the rescue.
Anybody know what the break-over angle is with air suspension on very high?? Our driveway angle from the street is ~12 degrees, and we have good friends that have a much steeper driveway we'd like to be able to get in as well...
 
Anybody know what the break-over angle is with air suspension on very high?? Our driveway angle from the street is ~12 degrees, and we have good friends that have a much steeper driveway we'd like to be able to get in as well...

Air suspension at 6.4" will give break-over angle of 12.5 deg
Note that tire pressure and passenger/cargo weight will influence the above estimate. Suggest you make yourself a cardboard mock-up with the 180 deg - break-over angle and measure the driveway first before your first drive to be sure.
 
I'll just leave this here:

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No, no need to feel at all disappointed. I owned a Model S with it and now own a Model S without it and as far as normal driving goes, I have not noticed any difference. I may of felt differently if I had to drive a lot over various high bumps in the road or driveways, etc. But from a ride and drive standpoint, if there is a difference, it is minuscule. Enjoy!