What would be the best headphone setup (Amp and DAC as needed) under $500 for everyday use (gaming, office work, movie watching, analytical listening, fun) for the aspiring audiophile?
Clarity, details, imaging, soundstage, comfort, scaling, build quality etc. would all be considered.
(Sorry if the question is very vague or hard to answer I am still learning about audiophile equipment but I am very interested)
Hello.
Have you considered headphones that not need a stronger external amp/dac?
Can highly recomend Dali io4 or io6, depend on you want anc or not, great build quality, but they was little too tight for my head, play very open and clear.
B&O h9 3gen is also in this price range, sounds very close to dali but they have more bass, and they have more aluminium then dali, the leather is real, and the head pillows feels very soft.
You can download the B&O app and adjust the sound the way you want it to sound, and the adjustment saves on the headset so it’s for all units you use them on.
Best would be to visit a store and find 2-3 different types you are considering, some would fit your head and ears better then others. Take your time, use your own phone to listen to music that you Are used to hear when trying new headphones.
Hi and welcome HFGF 
the Beyerdynamic DT880 600ohm is great for gaming, fun, detailed and comfy with great build quality, pair it with say an iFi Zen Dac and a iFi Zen CAN this would be pretty great and almost on budget 
in regards to office work do you work from home or are you going to an office and travelling currently?
A good V shaped Phone are the Emu Purpleheart from Massdrop for 75$.
And paired it with the Ify zen Dac it is enough with a solid good Soundstage.
Hi! Welcome to HFGF! I’m assuming this is a desktop setup. I mostly agree with @Ohmboy but would recommend swapping out the Zen CAN for a Schiit Asgard 3 if you live in the US. That’s because I agree with him that the 600 ohm version of the Beyerdynamic DT880 does well all the things you listed as wants. The Zen Dac’s bass boost routed through the Asgard 3 gives the bass-lean 880 more low end heft when you want it, too. If you buy everything new you’ll be just over $500. Deal hunting or buying used can get you back under.
The classic choice if you have access to Drop is the HD6XX + Schiit stack… or any good ~$200 dac/amp setup. A good number of people just stop here - good for them since they won’t be wasting more money on this hobby like the rest of us. :^)
Also worth picking up a KSC75 at any point in your audio journey. Doesn’t have sub-bass, is built cheaply, looks really stupid, but is most definitely worth the ~$15-20 if you want good treble tuning. Low commitment purchase.
Thank you everyone for being so helpful and welcoming!
To answer the questions that have been asked: I work from home and yes, it is all desktop work.
Additionally, with my experience with headphones, some are not as comfortable for glasses wearers. What can you say about the comfort for someone who wears glasses?
I have also been watching @DMS and @ZeosPantera reviews to get a better understanding of the options at this price point. Recently, @DMS had made a “ranking” of the top headphones under $1000. After studying from these sources, I was looking at the hd560s and harmonicdyne zeus (I have heard the zeus does not require an amp) in addition to the DT-880 600 ohm and hd6XX mentioned.
Which would you recommend? How do these compare?
Thank you again for all the help!