Ehhh, I'm ballin on a budget, so take that into account.

Generally, if I really want to sink into the music, I'm going with either my lgg7 and my beyerdynamic 770 80 ohm; or whatever device can connect with my usb DAC, a fiio q3.

I do have other options, but that's my main listening because I simply don't have the budget to do a proper system with how little I get a chance to listen to music away from headphones. My computer has a decent sound card, and some klipsch speakers that aren't bad. There's a home theater unit with cd/bluray hooked up, as well as the shieldTV, and the ability to connect via Bluetooth or cable to whatever device I prefer.

My car is decent, but not audiophile level. More bass focused than anything else.

I do have other headphones. Some tin t2s, some sonys, an old set of koss, that kind of thing.

File wise, its flac and opus.

I use poweramp and/or usb audio player pro. I prefer poweramp, but the other does bit perfect, which I do like on occasion, and it's more DAC friendly.

I'm happy with the options I have, all considered. Most of it was picked up either on sale or used. I would save up while shopping, then get the best I could get when I was ready. But the key to me is that when I want to, I can listen to anything I have and hear the nuance of it. The sound is as clean as I can get it on my budget, and in all reality, my old ears can't make use of anything fancier.

You spend almost fifty years living and listening to it loud, you aren't going to get much bang for your buck out of the really high dollar, precise gear. Hell, I can barely tell a difference between lossless files and mp3 om any given listening method. It's there, I can still hear a difference, but it's barely there for me. The better gear helps, but not enough to keep upgrading for tiny changes.