[guyben]

Well,
I am being offered a very generous gift of ~5000 dollars by a family member to celebrate a substantial event in my life. And what's better than to spend it on audio equipment.
This will be spent on head gear as I do not have the space for a good speaker system.
I mainly listen to classic music but occasionally vocals and some jazz.
Currently own a simple set of Oppo Ha-2se and a b&w p7, which I do like.
I am looking for suggestions of setups (dac amp headphone) up to 5000 dollars which will give the best results for my listening preferences. Source is flac and high res files from my computer. Importantly - equipment can also be bought used.

Thanks everyone!

 

[headphonatic]

Are there any local audio stores? if not just order a bunch of crap off Amazon and if you dont like it play around with it or return it. Personally I'd try to find a used Stay SR-009 on the classifieds and a used kgsshv.

Also there's a reccomendations section but I've never seen a request as hefty as yours.

 

[leonnoelimagery]

Congratulations on your accomplishment! 5 grand is a huge chunk of change to spend, I don't think my recommendations are gonna blow the entire budget. Considering that you mentioned the Oppo HA2-SE, I'm assuming that your source is digital from a computer or some form of transport. Also, you mentioning that you are looking for an alternative to a speaker system due to space constraints therefore I'm gonna suggest open backed headphones. 
 
DAC/AMP
 
Fostex HPA8 MKII (DAC/AMP); One of the best DACs for extracting detail from sources, and very flexible IO. I love the button in from which allows quick switching from RCA out in the back and the dual 1/4" outs in front if you want to hook small computer speakers to it. Downsides for it though is that it's super heavy therefore not very transportable and the DAC section doesn't work if you don't hook it up to the mains.
 
Ressonance Labs Concero HD (DAC only); This one is more musical and is powered by USB and has a very small footprint. Doesn't have the flexibility of most DACs at this price range as it only has one set of RCA outs and USB/COAX inputs. 
 
SPL series of Phonitor amps (AMP); All requires mains power. They have the best crossfeed function and the bigger (more expensive) the amp the more ball and whistles you have, for example, a balanced output. This would replicate the "speaker system sound" that you're striving for. The entire line of amps can power all headphones that I know of, discounting electrostatics.
 
Headphones
 
As I have recommended solid state amps, for detailed extraction of musicality, I'm going to suggest laid back headphones to achieve the relaxed to calm the natural analytical nature of solid states.
 
Audeze LCD3; I love it for the accurate bass and detailed treble. Not too difficult to drive if you so decide to switch it up down the line with different amps. This however has a V shaped sound signature there vocals would be slightly recessed. For long listening sessions, I find this headphone a little heavy, 2 hours maximum for me, creating a hot spot where it rests on top of my small head. I look ridiculous in it. Oh, also this one would blow approx half your budget. 
 
Focal Elear; Half the price of the LCDs with albeit more punchy low end and dynamics. It's sound signature is similar to HD650, if you ever auditioned those, but more dynamic and better low end, overall clarity and soundstage. Hands down, one of the most comfortable headphones considering it's weight and size but the only thing annoys me is the long heavy (but quality) cable that comes with it.
 
Senheisser HD650. I don't think that this headphone needs any explanation. This is my personal go-to-sleep headphones, lightweight and comfortable with a soothing sound signature.
 
 
Well, that's my suggestions and I would love to hear what you think of it and ultimately what you decided to get. You'll also have change based on my suggestions where you can spend some of it on upgrade cables for your equipment.  

 

[sheldaze]

Congratulations!
 
But I must be up front - it is an interesting price point. Whereas you could get a TOTL headphone, such as the LCD-4 or Utopia, you'd not have funds remaining for what I would think to be the best compliment to that headphone. Or you could get a TOTL system, such as Hugo TT or any of a number of competing amplifier and DAC pairs like the Ragnarok and Yggdrasil. But you'd end up with the same issue, being stuck then with an Elear or a comparable headphone at that price.
 
In my opinion, the sweet spot for headphones is between $1000 and $2000 dollars, with a few options below $1000 too that can be complimented by a proper front end foundation. But you will need to find the headphone that best suits your listening preference first! Find that headphone that suits you, and build the best possible system around it, and you will have what amounts to a TOTL system.
 
This is not an endorsement - just a personal example. I like the HD800S, but it can be a little bright. I have found, for my preference, connecting it to a Carbon to work well for me. That would allow me funds to get a reasonable, very high end DAC, such as a Holo. Or you may be surprised to find that the HD600 or HD650 work well, when fed by a very good amplifier. I think I enjoy more these cans fed from an Eddie Current Zana Deux Super, and a reasonable DAC like the Chord 2Qute, over the small sonic difference between the HD6xx and the HD8xx lines. In my opinion, using a reasonable headphone, fed by a very good system, can overcome its slight sonic deficiencies and make for a very rewarding system.
 
The key - find your cans. Then build your system around it.

 

[Me x3]

You need to know which kind of sound you want in order to pick the right headphone.
Once you're over 900usd most headphones are very good in different ways, so you won't find one that's much better than the others. Just different. You don't even have to spend all your money. You might like an Audeze LCD-2 more than a Stax SR009.
 
More often than not people will tell you higher price tag means higher sound quality, but my advice is to forget about pricing and focus on the kind of sound each headphone provides. If you can try them out, focus on enjoyment. If you can't then try to find non hyped reviews describing the sound signature with pros and cons. Every headphone has pros and cons.
 
Once you've picked the right headphone, start thinking about source and amplification.

 

[nvfan]

Put as much as you can into the headphones is my suggestion.

Some audition suggestions:

Stax SR009
HD800 (super dupont mod)
Focal Utopia
He1000v2
Stax SR007
MrSpeakers Ether Electrostats
Sonoma Model One
Audeze LCD-4

 

[Jon773]

Second hand is a good idea. You should be able to pick up a Hifiman HE-1000 v1 and an Auralic Taurus MkII and a Vega for reasonable money second hand.