Yes to the second part, but heck no to the first part. Something sounds great until you hear something better. Further, my more experienced friends who habituated the high end shows mostly noticed how the expensive, hyped stuff did not sound nearly as good as far lesser priced gear they already knew well. Exceptions were few.
And to hopefully still the silly chorus, cables, DACs, megabuck sources and other sideshow high end stuff will not make an amp, headphone or speaker better. If you want improvement, seek out a better sounding amp, headphone or speaker.
Most importantly, if you want to improve your musical enjoyment, listen to better music. That is WAY more important than what gear you hear it on. That is no more or less subjective that what high end is! It does not matter what genre of music you listen to; find musicians who do it better than what you are listining to now.