
Sennheiser
HD 560S
Budget gaming king with clear sound, but tight fit.

Running these analyses costs money. Buy through my links to help keep lights on! I may get a small commission.
Oh man, thanks for making me feel somewhat normal as have 5 different ones here. AirPods for travel and podcasts Beyer dt1990s for work Beyer dt1770 for home Logitech G Pro x2 for the mic and gaming Sony MDR 7506 for when I don’t want to bring out the big boys, or they might get damaged.
I do find they’re very revealing in the upper midrange which can be generally interpreted as harsh. I’ve used them for years, & do find them accurate, especially for guitar & vocal frequencies. If they are sounding harsh to you it might be that your ears are more sensitive in those frequencies or that your rig has more cut than you realize. That being said I find the Audio Technica ATH-M50 more forgiving, and use them more often for headphone practicing. I still like the Sony’s for things like monitoring a full mix for live streaming. In that scenario having extra detail on the guitars & vocals helps.
I'm an audio nerd and have friends who work in radio. My total overkill setup (assembled during COVID) is this: Electro-voice RE20 mic on an OC White mic arm, DBX 286s mic preamp/processor, Henry Engineering USB Matchbox interface, random headphone amplifier, and DT990 headphones. This setup is totally reliable, and everyone says that I sound great. You could go with a much cheaper mic, like an SM57, and still sound great. If you prefer closed-back headphones, the Sony MDR-7506 would be a good choice.
Got one and bunch of studio monitor speaker. To be honest, no better than normal headphone.
for travel I'd lean towards iems over closedbacks and generally offer better sound quality for money with more different tunings available. *Alot* of banger iems from 100$-$200 but heres a run down of the better closed backs if you want to stick to them. fiio ft1 which sound amazing but are on the thiccer end could be an option if thats okay, akg k371 sound nice but don't have good build quality, Sony mdr7506 great but very neutral which I generally wouldn't recommend a beginner blind buy for
Sony M1 and MV1 doesn’t need amp. MDR-7506 will do if you want affordable. They are all studio level clarity and accuracy.
Classic Sony MDR-7506, AKG K361 from your list. Wire usually has better sound than wireless (convenient and noise cancelling). I would not risk sweat on them for light running, the smell stay on earpad during your long study session.

Sennheiser
HD 560S
Budget gaming king with clear sound, but tight fit.

Sony
WH-1000XM4
ANC king, durable, but unreliable mic and touch controls.

Sennheiser
HD 6XX
Legendary mids, durable, but narrow soundstage and weak bass.

Sennheiser
HD 490 PRO
Super comfortable, wide soundstage for gaming, versatile pads.

Sennheiser
HD 599
Super comfortable, easy to drive, wide soundstage, open-back.

Ranked #1
Sennheiser - HD 6XX

Ranked #1
FiiO - FT1 Closed-back Headphones

Ranked #1
Sennheiser - HD 560S

Ranked #1
Sony - MDR-7506

Ranked #1
Sony - WH-1000XM4

Ranked #1
Sennheiser - HD 560S