What do you guys do most of your listening on?
I generally stick to my M-Audio BX5's. Pretty solid monitors for the $200 I paid for them. Bass extension could be better, but they're just 5's. I'm debating on whether to get a sub or just upgrade to 8's. They're about the same price, but one is much, much easier to set up right. I hate fucking with subs man. No matter what you do, it's hard to get a good, matched and balanced sound from a 2.1 setup. Better to have two speakers with balanced bass extension and roll-off.
For headphones, I have a pair of Sony RH-5Ma's which actually aren't bad for cheap beat em up headphones. Those are the ones that leave the house.
The serious listening is done with my trusty Audio-Technica ATH-M40x's. They're clean and balanced... ...a little scooped, though I think they do fill out the midrange pretty nicely... ...probably just two narrow dips at 400-800 and 3-4k, which I think is actually more desirable - lessens fatigue. Being closed-backs, there's really no soundstage to speak of, but the bass extension is great. Very clean and responsive low-range. I like that I can hear the dynamics of every performance... ...all of these little nuances in the attack come out through them. You hear every little scrape of the pick, every ghost-note on the snare, every slip and slide on the fretboard, every breath the vocalist takes... ...they're surprisingly detailed for $80 cans. I always look forward to putting those on.
I really need to upgrade my out-in-the-world setup. I usually just use my phone. I should at least get one of those little pocket amps. At home, I run my headphones into a Scarlett 2i2 USB interface. The DAC and headphone amp are actually pretty good on that little box.
I try to keep it all pretty cheap. I don't trust myself with expensive equipment.