I wish I hadn’t have discounted iems, since I now use them much more than my over ears, even when I’m at home. I also wish I had have had a better understanding of the type of sound signature I preferred, would have saved myself a lot of time and money. That being said, I did enjoy the journey itself to finding my end game 🙂
Get a DAC. As they say in the coffee world, the grinder is more important that the machine. The DAC here is more important than the IEM’s / Headphones. Obviously don’t buy a DAC more expensive than the headset, but get a good one.