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I don't think anyone is going to feel bad for me if I missed AP 2.0 by a few weeks. Myself? Hell no! I waited long enough and once I decided to buy I am now looking ahead with no regrets no matter what comes next. Besides it's a lease and I will get another S in 3 years
While true Tesla does soften the blow with their free software updates, with actual, new functionality.
So for the components with the shortest timescale between improvements, namely the software, you don't get left behind with a Tesla (as long as your hardware supports it, naturally).
This is an uncommon if not unique trait among car manufacturers.
What would be truly awesome is if Tesla would standardize on an option to trade-in the battery for a new with larger capacity (since the battery technology is also undergoing improvement at an exponential rate).
Lease a car and after 3 years buy it. Then decide you want a bigger battery as well. Just swap and you now have 100 miles more range, cool. It's the same battery configuration, why not? I like it!