I've noticed this trait with myself in a number of other aspects (operating system--no way I'm going back to Windows after having used Linux for years!), but luckily I haven't been spoiled by other people's good audio equipment yet.
If you haven't gotten into high-end audio already, I'm guessing you're not the type who "listens to equipment" as opposed to listening to music. So long as you're paying more attention to the music than the minute differences between exponentially more expensive pairs of headphones (or DACs and amps), you're probably not going to have the problem you're afraid of. I can rarely hear the difference between my midrange Sony wireless headphones and my friend's super fancy open-back headphones when there's an equalizer profile applied to each to make them sound similar.
If you haven't gotten into high-end audio already, I'm guessing you're not the type who "listens to equipment" as opposed to listening to music. So long as you're paying more attention to the music than the minute differences between exponentially more expensive pairs of headphones (or DACs and amps), you're probably not going to have the problem you're afraid of. I can rarely hear the difference between my midrange Sony wireless headphones and my friend's super fancy open-back headphones when there's an equalizer profile applied to each to make them sound similar.