I have a bit of experience (just a pair of iems and a FiiO dac/amp) and I’ve noticed that, no matter the equipment, always enjoy you music for many years I listened my songs with a cheap earbuds and my phone, and just this year I could buy my dac, and my iems are not pricey, they were 35 bucks, plus the dac, I spent 100 dollars, and was the best money I could ever spent, listen to what you like, everybody will say that you should listen to “audiophile” songs or less mainstream music, just crap, even if you just have mp3, they’re yours, and if you enjoy them, it’s awesome, I don’t have many mp3, but they’re mine and that doesn’t mean that it’s bad music, and always buy gear that you can afford and you’re comfortable with, for example I prefer a portable dac, because I like to listen my music on the bed or my desk, and overall, sit down, relax and enjoy, and don’t get overwhelmed if you want to upgrade and get the best value, just buy something that is well known for its Qualities, even if it’s a bit old, you won’t be disappointed, for a reason that gear it’s well known