Should I upgrade my headphones or my Dac/Amp?

It's been about a year and a half since I got my Beyerdynamic DT990 Pros and Fiio E07k/E09k combo. Now I am looking to either add to my headphone collection or replace my Fiio gear. Which would you all recommend I do first? I have a budget of 150-200 dollars.

I am really happy with my DT990s, but would like a pair that are more balanced and less bass heavy. Not sure if I would be able to find a Dac/Amp that would be better than the Fiio in that price range, but I am open for suggestions.

I'm looking at the DT880 Pros, but am willing to look at other brands.

Replace that Fiio gear, cheap precises of crap!
(Sorry I've just had too many problems with their "amps" and "dacs")
DACs can greatly change the sound signature I'd look up some reviews for some in your price range and hear what people have to say about them.

A better pair of headphones would do you better. Getting a new dac/amp will not really change the sound signature significantly unless you grab a dac with a ton of distortion or some cheapo amp.

better dac and amp definitely.

We can help you address the bass issue later on, but you need better gear first.

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I got the fiio e17. It's really nice and I like the portability and battery life of it.

I mean I don't quite understand what about your setup you don't like. I have a Fiio E10k and a pair of Sennheiser HD518s and I have no urge to upgrade at all, the sound is great and clean. If you want a different sound signature then maybe buy a different pair of headphones but any upgrade to your DAC/amp is verging on placebo.
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What do you want out of an upgrade?

Upgrade your Dac/Amp to get more out of those headphones.

This is a popular setup that will breath new life into your headphones. The Dac is widely regarded as the best in it's price range.

Dac: Schiit Bifrost Multibit ($700)
Amp: Schiit Magni 2 ($100)

That dac is too pricey at the moment, i have a $200 budget. I did just purchase a pair of Fostex T50rp mk3's for $130 to use (impulse buy), and I forgot I do have an Asus xonar U7 which has a good dac. I guess all I need is a better amp than the Fiio?

I have looked at the schiit, also are there any decent tube amps in this price range?

I still don't quite understand the goal here except to just have more toys. If you really need more power I don't think you should spend anything on crazy things like the Shiit audio stuff or tube amps, you will be literally just burning your money on markup and hype.
The O2 Amp from nwavguy is manufactured by Mayflower Electronics, the Tek has had them on several times. This amp is powerful and clean with almost no distortion, this is the goal of an amp. They also have a version with a built in DAC if you think your Fiio is somehow not good enough.

Spending money on tube amps is crazy, if you like warmth get some headphones biased towards warmth. Sounds like you have quite a few headphones, so you should probably want as neutral an amp as possible so you can really highlight the differences between them.

Also can someone explain to me what the hell a $600 DAC is doing to cost $600!?

A rule of thumb I've always followed is that the closer it is to your ears the more important it is. Example: CD player=least important. Amp=more important. Loudspeakers=most important.

I know it's a debatable statement. Special cases will prove it wrong, but as said, it's just a rule of thumb.

Tube amps aren't "better" because they look cool. Tube amps are actually "worse" by definition since they will always color the sound in some way. It's this "coloring" and distorting that people like the sound of. It's all a brain thing. It's typical for older guys to like tubes since the sound of them makes them remember the days when they were younger and had better hearing. (the stereos and tvs when they were young all ran on tube amps) It's pretty rare to find young people who actually like the way tubes sound in a blind A/B test.

That being said, I have always heard+read that tubes aren't worth getting into for less than $2000 unless you plan on building it yourself. Even then, you should do some blind A/B test with somebody else's amp to see if you even like the way it sounds. (It's going to be warm, distorted, have a wonky EQ response curve, terrible SNR, lots of hiss/hum and some buzz.... this is the nature of tubes)

Thanks for all of he recommendations guys, I just put on my T50Rp mk3's and am blown away with the sound! I do want to upgrade my amp, but I am pleased with the Dac in the Asus U7 over the Fiio.

These things are hard to drive though, I have my E09k almost at max volume just to keep them at a normal listening volume.

I use the fiio x3 1st gen as a dac and it's great. I don't know what your talking about. Have you tried using a line controls with the dac's?