It's a pretty polarizing subject. I am in the "just check all my crap and be done with it" camp, but many people you'll have to pry their roller bag carry ons from their cold dead hands.
If you have expensive electronics or a controlled substance prescription, you're a fool to let them pry your bag from your hands. United recently forceably checked my carryon bag (because I hadn't paid extra to be in a lower boarding group) on a long international flight (multiple connections) where I would be without my belonging for 40 hours. Pretty rough when you will start going through withdrawals after 8 hours. It was like the end of the scene from Planes, Trains, and Automobiles where the car rental lady (after receiving abuse from Steve Martin's character, which didn't happen in this case) coldly tells him, "you're fucked."
I have a backpack that fits in the overhead. I don't pack more than will fit in there. My personal item is usually my work laptop, not letting that go. I see no reason to check anything.
Yeah, I am with you on this one. And even with that worst case scenario dodged, checked luggage experience just sucks.
After landing, instead of just up and leaving the airport, you gotta go to your baggage claim and wait for your flight to get processed. Sometimes it easily adds over an extra hour to the experience (and even the best case scenarios still take me about 30-40 mins extra at least, and that’s domestic flights).