The biggest benefit in sound is in the transducer (headphone/IEM). But once you hit a certain standard in transducer quality, it might be wise to invest in a good amp to future proof your hobby. You don't need to buy a good source every few weeks and one good one can last years in this hobby.
DACs are generally quite similar in measurements and sonics nowdays, so I would put most money in the transducer first, followed by a one time expense in a good amp. Then perhaps the DAC next.
I think to start the most important thing to get locked in is your headphone(s), with the balance split between an amp and a DAC.
Once you get further along in the hobby, there are definite gains to be had by upgrading not only your amp and DAC, but also your source as well.
I have 5 HP amps, ranging in price from $100.00 to $3800.00. There is a definite improvement in higher end amps, but the law of diminishing returns does kick-in.
Similarly, I have used DACs ranging in price between $300.00 and $8000.00. Same story as with the amps. You will hear a difference between DACs once you hit a certain price point, but after awhile, it boils down to personal preferences.
Eventually getting off of a PC as a source and moving to a dedicated server and/or streamer will also result in better SQ.
2K only? I would go with the Ripper2860 Decware Tiny Radials setup (Thanks again Ripper for the advice on the Tiny Radials setup!). Tiny Radials is averaging about $569 (could get it less if someone makes it for you, I won mine from a local Schiit meet) > Cheap $100 Subwoofer > Schiit Rekkr ($149) > Nitsch Magni Piety ($165) > Cheap DAC of your choice > Source of your choice. That is about $983 before tax, so hitting a little over $1000 after tax and shipping. That leaves $900 of a DAC of your choice and source. Source could be a cheap dedicated CD transport under $400 or an affordable turntable like the AT-LP120-USB ($300) with a good cartridge ($199).
Schiit is probably my favorite entry-level equipment. The next best thing is to get a DAP with a good IEM to over portable. Under 2K, nothing beats a decent speaker setup for me with a CD player. Headphone route, I remember I used to like using the Sennheiser HD600 with the Cobalt on my computer (not recommended, but ignorant was bliss during those times). Those were good times... You could probably find a good cheap tube setup with the Sennheiser HD600 for under 2K and I would be fine with that as well.
Even average phones sound great out of a good source. My journey in that hobby taught me that source (dac/amp) is the most important thing in your chain, foundation for growth, phones come and go, some cheaper, some more expensive, but good source can stay for years.
My first the most disappointing experience was shelling out big chunk of money for HD650 and trying them out of laptop HP output. I know, cringe.
Having said that, times change, IEMs (if that's what you are after) can be driven to full potential by portable amps and dongles these days.
So if you go for mobile IEM setup, USB dongle like L&P W4 can provide exceptional SQ value for the money.
For big boys (full size HPs), I'd focus on source and amplification first.
Even average phones sound great out of a good source. My journey in that hobby taught me that source (dac/amp) is the most important thing in your chain, foundation for growth, phones come and go, some cheaper, some more expensive, but good source can stay for years.
My first the most disappointing experience was shelling out big chunk of money for HD650 and trying them out of laptop HP output. I know, cringe.
Having said that, times change, IEMs (if that's what you are after) can be driven to full potential by portable amps and dongles these days.
So if you go for mobile IEM setup, USB dongle like L&P W4 can provide exceptional SQ value for the money.
For big boys (full size HPs), I'd focus on source and amplification first.
Anecdote: once upon a time, I auditioned most of my local hifi store with a tiny DAP that relies only on onboard ESS DAC, no amp stage. Yes, I can hear improvements between IEMs, but nothing dramatic, so I was all smug “told ya, diminishing return”, (though I did buy a kilobuck to “end game”). The differences were much more dramatic when I came back much later with a proper amp or DAP. Still annoys me that companies don’t do a good enough job with engineering that I need an overpowered device to get the most out of mere IEMs.
If there is place where “kilobuck killers” appear, I think DAP and DAC/amp space needs it more than IEM space.
Traditionally in HIFi, it’s always been the source is the most important, followed by amplification and then the speakers/headphones.
However, years ago, you could get some very poor sources, like bad tape decks and awful record players. It didn’t matter what amp or headphones you used, it was never goig to sound good.
These days it’s a bit different, most of us have access to at least a reasonable source in the form of a mobile phone. If that’s all you want to use, then upgrading to a nice pair of IEMs can see a huge improvement in sound quality. The source will become a limiting factor at some point, but that all depends on how much you want to spend…
I only recently started using a Fiio BTR7 with a phone/iPad etc, but at this point would still spend more on headphones…
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% with Andrew_WOT !! Source equipment is key. If elements of sound are missing ‘upstream’, nothing ‘downstream’ can fill in / repair the gaps. 
