A range of 2,500-3,000 seems to be a good fit for me. I'm a 5'9" adult male with a light workout schedule.
I don't expect labels to be 100% on target but I do expect them to be close enough for my rough estimates.
The food truck may not list the calorie count for the burger but I've probably eaten all the ingredients in the burger before. From experience of noticing nutritional content in the past, I can tell if it has more fat (lots of mayo, extra cheese), sugar (ketchup) and overall calories (heavy, overall size of the meat patty) than ones I've had in the past.
The caloric content is not the only tool, it's one of the many tools you should have when trying to keep a healthy diet.
Yes, absolutely, everyone should do this (I certainly know how many calories are on the label of most things I eat). But you aren't counting calories.
Is it that you can't do it accurately? That seems to be implied by the second two questions. I haven't found that accuracy actually matter that much; mostly what's important is nominal calories over time vs. weight/other health indicators over time. If the number's not technically accurate, I kind of don't care. All I know is I roughly ate so many calories, my weight changed by x amount, and I can walk x far without getting tired. Over time, I can have a pretty good guideline for the number of "back of the box" calories I should be eating to reach my targets (which addresses your first question of "what range to target")
You mention explicitly that most people won't do it over the long term, which is definitely relevant. But even doing it for a little while can give you a good baseline so you can at least make educated guesses as to what you're eating, which is especially helpful in the "food truck burger" scenario.
I guess my point is that we all agree knowing roughly how many calories you're eating is good, but the only way I know to figure that out is to, at least for a while, literally count them. There's still a huge margin for error, of course, but if I didn't keep tabs on it by looking at the back of the box, I'd have no idea at all.
Counting calories temporarily tells someone how much he is overeating, but the problem is the amount he eats is an ingrained habit. Habits die hard, eating less for a couple months doesn't change anything for most people. There is a lot of evidence that most people who diet put the weight back on because they took temporary measures to lose weight instead of making deep lifestyle changes. [Anecdotal evidence alert]: making deep lifestyle changes was one of the hardest things I've ever had to do, and I believe counting calories would have distracted me from that goal.
Whatever works for you, go with that. But weight and body fat will fluctuate naturally and shouldn't be a huge factor in how you decide to eat. You could eat all kinds of crap that would keep you low-weight and low-fat but wreck your body.
Limiting yourself to reasonable portions of healthy foods 85% of the time is the easiest way to keep a long-term diet. Want pizza and beer? Save it for Friday night. It can't get simpler.