Agree w/r/t infrastructure: Tesla has invested a lot in the US to make it work. Think about going back to the early 20th century, before there were petrol stations on every corner. You’re starting to see more infrastructure deployed in car parks or even on city streets, but until there are more supercharging stations road trips will be tough. But the Model S has 230–250 miles of range, and the 3 is targeting 200, and statistically that should be enough for most commuters even without being able to charge while parked at the office. There aren’t many people with >100 mile daily commute s— that would be ~2 hours each way, assuming travel at highway speeds.
W/r/t upgrading: I think people will trade up to a newer model if there are significant hardware updates — e.g. full autonomous driving. Tesla could probably offer it as an aftermarket add-on, but I doubt it would be as aesthetically pleasing as having it designed into the car from the start.
About your final point — I don’t think most people who buy cars these days car that much about how a car drives. Most cars are designed for comfort, safety, and convenience (storage space, etc.). The best selling car in the US in 2015 was the Toyota Camry, followed by the Corolla, followed by the Honda Accord. (Source: http://www.caranddriver.com/flipbook/10-most-cars-here-are-the-bestselling-cars-in-america-for-2015#11) None of those cars drives “well” from the perspective of someone used to a 911, a Lotus, or even a Miata. But they’re perfectly sufficient for most people. I had to drive an SUV on vacation a few years back and it felt like piloting a motorboat through a lake of pudding, but that doesn’t bother most people. They just want to get to their destination safely and reliably. Driving enthusiasts — and I include myself in that group — are a shrinking group, but I don’t necessarily think that’s a bad thing. I’d feel much safer if every car was on autopilot — unless you go to the race track.
Thanks for all the feedback on the post!