Certainly when it comes to high-fidelity sound reproduction, the cost/benefit curve bends upward at a dizzying rate, so bargain-hunting is the order of the day if you're cursed with good ears.

Bose is generally overpriced plastic junk. No exceptions that I'm aware of, except for the mid-sized speakers they originally made in the '70s that made their name. But they haven't made anything great since then. Don't know the other brands you mention.

I like over-the-ear headphones for a multitude of reasons, not least of which is that I can more easily hear if a kid is having a meltdown elsewhere in the house. Plus I have a hard time regulating volume with in-ear buds. I get the volume way too high without noticing; something just goes off with my ability to gauge loudness when I have pencil erasers in my ears.

I know that stage musicians get in-ear monitors of the highest quality, and they craft them from actual casts of their ear canals. Expensive, but worth it if you're paid to be onstage and on-key. How do these modern in-ears work? Do they have a selection of ear-canal fit bits, or some sort of flexible super-material that lets them fit any shape of orifice?