Well, lucky me my ears are REALLY average like if you ask someone to draw an ear, that's mine. For my headphone choice, I already committed to the Hifiman edition XS, and I'm sparing for the Fiio K9 pro to replace my amp. Still wondering if the K9 pro isn't a bit too much but that amp is universally acclaimed and doesn't cost an arm and a leg.
Can't really offer any advice on the Fiio, since I've never used one. Your comment above about it being universally acclaimed sort of begs the question though... for what? Is it the sound quality, features, connections, portability, or maybe something else?
Again, I'm not that familiar with the Fiio product line, so I don't really know much about them.
My biggest problem is for the speaker and speaker amp that are quite the nightmare to figure out and as said by @LTig , there's a ton to learn to be able to choose confidenlty.
Maybe yes. And maybe no. Like anything else, audio enthusiasts sort of have their own language, and shorthand for alot of stuff. Which can be a little intimidating at first. Most people are more than willing to lend a hand though, when asked. And the basics of a good stereo speaker setup aren't really all that complicated... Unless you want them to be.
Rather than diving in headfirst with alot of different gear, my advice would be to start simple. And then build out from there. There are alot of folks who don't have the discipline for that though. And want all the bells and whistles from the get go. Which is fine too, I guess. If you have the wherewithal for that.