I was saving up for the HD600 when impulse-bought these dt880 when I found them used for $160. (not as good a buy as I first thought. It came without packaging/case/accessories, so there's not much resale value left in these, i might as well hold on to them).

I do like them quite a bit. I don't think there's enough wrong with it to merit replacement just yet. I don't think the treble is that bright. I'm not trying to fix something intolerable, I'm trying to fix imperfections. There's a lot that I love about the dt880s. Also, I feel like sticking with these because these are 600ohm, and I keep thinking that I haven't really seen what they're capable of.

Now i'm kinda stuck, reassessing what I really want.

I could either get a decent solid state amp for these and get some sort of an equalizer. Or I could get a tube amp and try my luck tube rolling.

Getting the hd600 and an amp right now is a huge expense and not something I can afford right now, even if I were to sell my dt880s for whatever I can get for them. Plus, I know that this is kinda odd to say, but at this point it doesn't feel like the hd600 is enough of an upgrade for me to actually bother. I know that I prefer their presentation better, but idk, some part of me wants every next headphone to be a significant upgrade, not a mere sidegrade.

So thats where I'm at. My instinct is to buy a good amp (for around $200) right now and hold on to the dt880s and keep an eye out for used hd600s.

Maybe you can get a used matrix mstage or hpa-2. They're a warm sounding solid-state that will probably do well with the hd800s, plus you can roll the OPAMPs for more flavors. The original valhalla 1 is supposedly much more tubey sounding than the V2, which may be right up your valley.

I don't think this has been asked, but what dac are you using? Cause that can make a pretty significant difference as well.

My dac is basically whatever my laptop/ipad's inbuild soundcard. I do plan to upgrade that too.

I've been told that the dac is the least significant component in the chain (when compared to headphones and amp), so I was hoping to get to it last. Also, I'll want a separate headphone amp, because I'll be buying a focusrite 2i2 for recording purposes, so I'll have to use its inbuild dac (right?).

The exchange rate has really made it hard to find things at a good price in canada over the last year or so..

Ah another Canuck joins the fray.

Onboard sound is really really terrible. My laptop can't even handle stuff past 10kHz without hilariously bad distortion.

The 2i2 will be sufficient for your dac and amping needs in the short term though (I have a Focusrite 6 usb that works well enough).

There the hell are you getting your advice from OP?  OCN?!

Okay, just went back and did some research, i need to get myself a decent dac.

But i still need a good amp too. The cmoy isn't doing a good job driving the 600ohm dt880s. My volume is always turned all the way up.