Just wanted to chip in as someone who didn't have braces and doesn't regret it. I don't have perfect teeth, but I would say the difference between "my house looks like a hotel" and "clean but lived-in". You can tell they haven't been "braced" but I don't think anyone has ever actually called them crooked or ugly. And FWIW, I think they were worse when I was a kid, but straightened themselves out, mostly. I have bigger "problems" with staining from tea/coffee/wine (because putting whitening chemicals in my mouth seems gross) and and remembering to floss because I wasn't taught/required to as a child :(
However, OP, it sounds like your son's teeth situation is very different in that he actually needs it for health reasons (jaw and facial muscle development, ability to eat diverse foods, ability to clean teeth well, etc). That would definitely qualify as "worth it," where "it" also includes the extra effort to supervise hygiene habits. Which are important anyway...it's shocking how many adults don't brush 2x daily. Or even once.
Oh, and finally...haven't dealt with ortho offices, but I expect this transfers: my bf and I have different dentists (different insurance and we wanted offices near work), and our experiences were WORLDS apart. Mine was exactly what I expected, high level of care, lots of time with doctor...his...was administratively mismanaged and uncomfortable, although the cleaning and fillings seem fine so far. Basically: it matters.