If you're on a 400 mile road trip, you can drive the first 250 or so on a fully charged Tesla, but then you'll need to stop for a half hour at a Supercharger and let your car charge up to get the remaining 150 miles. If there's no Supercharger around and you need to stop at a conventional EV charger, be prepared to wait an hour or more.
Because of the non-trivial time increase once you go beyond the initial range of the car, I know I'd be less likely to want to take trips beyond it, even if they were technically doable.
Stopping for 20-30 minutes every 150 miles or so isn't a burden for most people. Some people really like to push. But you really should be stopping that long, that often, regardless of what you're driving. People don't always do it, but they should.
As I mentioned in a comment elsewhere, the impact of charging time really depends on what you do in that time. If you can time your charging to coincide with a meal, for example, then the actual penalty from charging is zero. If you're doing a 400 mile road trip and you can make your supercharging stop your lunch stop, then you'll lose less time to charging than you'd lose to filling the tank of a gas car. Obviously that's a big if and it's not at all guaranteed, but the point is that this isn't an absolute, and "30 minutes to charge" shouldn't be thought of as being the equivalent of "30 minutes to fill the gas tank."
Personally I love long trips in the Model S. Part of that is just because the car is extremely comfortable and easy to drive, which makes long trips much less tiring. I'm sure that would come with other cars in that price range too, so not something that's exclusive to Tesla. The extra charging time has not so far been at all an issue. I've made three trips beyond the range of the car in the six months I've had it, and my total time spent waiting for the car to charge is zero. I'm sure that will start to become non-zero when I want to do, say, 500 miles in a day, but I still look forward to longer trips in it more than I did in my previous cars.
Lack of charging at home is a big problem for sure. I would not buy a Model S if I couldn't charge it where I lived. Many apartment building owners are amenable to installing chargers, but many aren't.
Note that you don't necessarily need a garage, just dedicated parking somewhere reasonably close to electrical infrastructure. Houses with at least carports or driveways are pretty common places to live.
"Never take road trips further than 250 miles" needs a strong amendment. "Never take road trips further than 250 miles where charging can't be done at the destination and you're outside the supercharger network and away from CHAdeMO stations." Sure, it happens, but it's pretty rare. If you're staying within the Supercharger network, or you stay within one-way range and can plug in at your destination, then trips over 250 miles are no problem.