[Tranqville]

My current set-up: mostly FLAC source files, JRiver player streaming to JDS Labs Objective2+DAC at 24bit/96khz, HIFIMAN HE-400 (rev. 1). I just ordered angle pads from Lawton Audio and am in the market for replacement cable (my stock cable is literally hanging by a thread).  
 
I have been quite happy with my set-up, but the best is the enemy of the good, so I wonder how can I move up the ladder in my sound experience without investing a fortune. Ideally, I would get Audeze LCD-3, something like two Woo Audio WA-234 mono blocks, Naim DAC V-1, but those are way above my budget. 
 
I  don't know what to do next. What should be my upgrade strategy?  What is the weakest link in my set-up? If I budget 1-2k for improving my sound, how should I spend it meaningfully, with my goal for ultimate sound in mind. Or should I just wait and get a bigger budget to buy  things that I really want. Do I actually need those things? Will I be able to discern between 1k and 5k DAC? I don't have golden ears, but decent enough to hear many problems with my current set-up and wanting higher quality sound. 

 

[FourPlay]

In order for us to help you, you must define "a fortune." Without knowing your budget, it will be like playing craps.

 

[jodgey4]

It says 1-2k, mate .

I'd say put as much into the headphones as possible. Diminishing returns hits hardest on gear, as long as your DAC is clean and you have enough clean power from your amp. You could probably get the LCD-3's and have 98% of the sound quality of a $2k source just with your O2/ODAC.

 

[linglingjr]

Save money by buying everything used on here or other forums.  Lurk around the B/S/T and wait for deals to come up.  You're probably not going to notice much change going from your ODAC to a $500 dac.   I don't know how well the O2 drives the audezes, but if you want to give them lots of power for cheap people do power them with speaker leads from a receiver. That'd be cheaper than a more powerful amp (especially if you already have one)

 

[Tranqville]

     I don't know how well the O2 drives the audezes, 

I believe O2 is not powerful enough to drive HE-6, but matches perfectly with my HE-400. I don't really know how power-hungry LCD-3 is, but probably similar to HE-6. 

 

[Za Warudo]

The weakest link in your set up is the HE400.  Unless you are okay with the recessed upper mids and peaky treble (not to mention the weight), I'd recommend trying some other open headhphones.