For whole food, I agree that calories don't matter because we can trust our satiety signals. For junk food designed to be overeaten, I find that information quite useful.
Note that I do track my calories periodically.
In spite of popular claims it isn't that hard, technically speaking and it doesn't have to be super accurate.
The problem with calorie counting is one of mentality. Because you end up thinking about how many calories you have left, it ends up draining you emotionally and you can suffer binging episodes due to it. The brain is unpredictable and we can't necessarily control ourselves which is why we can get fat in the first place.
I think everyone should try to measure their calories for educational purposes. If you do, the best app is Cronometer, by far.
But to lose weight you need first of all long term compliance, so you need a strategy that can work long term. Counting calories doesn't work long term if you're too emotional and you can't help to treat those numbers as anything else than just data. Counting calories definitely doesn't work for me.