Interesstingly I love to listen via headphones since I feel to be more focussed and able to hear/dive into more details. But I don’t have any high end equipment or ever had…
Yes, Hifi is the one expensive thing I bought in my life (after convincing myself I could/should finally afford it). I chose my apartments for proper sund insulation too, so I could play at a good level. For orchestra music, the dynamic range is really big (esp at 24 bits) and when the sound is pure you have no idea how loud it actually is (until someone tries to talk to you). Loudspeakers can generate sounds/frequencies that headphones can’t, so there’s no comparison, but you need to have decent acoustics otherwise it doesn’t help.