I have not checked a bag in six years, and I intend to keep it that way. Every argument in favor of checking a bag falls apart under cross-examination, starting with "it's easier" and ending somewhere around "the airline lost it in Denver."
The case for carry-on only rests on three exhibits: a packing cube system that turns chaos into an organized filing cabinet, a merino wool rotation that survives five days without ever announcing itself to a conference room, and the simple fact that you are always first out the airport doors while everyone else waits at the carousel.
Opposing counsel will tell you that a carry-on limits what you can bring. I would submit that it limits what you feel like you need, which turns out to be considerably less than what you packed the last time you checked a bag and then wore four outfits out of it the entire trip.
The only exception I will allow: ski trips, and even then, I have opinions about renting gear instead.