Headphone + dac/amp recommendation

Hello, currently I’m using Superluxes HD668B with velour pads and while I’m satisfied with how they sound, they are not very comfortable for me after hour or two and I want to replace them.

Use case is like 80% gaming, 20% music. Over-ears. Comfort is no.1 priority, I’m wearing glasses.
Most likely open-back/semi-open, unless there is very good closed-back option.
Sound wise, as I said 668b are good enough so anything better then them is awesome.
I did quick search and my current picks are Philips SHP9500, Sennheiser HD559, ISK HD9999.
My max I want to spend is ~$80, is there anything else worth considering?
Which one from these 3 above?

Now, onto the DAC/AMP. Currently I’m using Asus Xonar U3 sound card. Is there any point switch onto something like Fiio E10K? Will there be a noticeable quality bump in audio justifying purchase?

The shps are good, competent for gaming.

If you want extreme comfort, the CoolerMaster MH751 would be great. Also good for gaming and has a detachable mic.

What about something like the Sennheiser HD58x? Would be a big step up in quality for gaming and costs about $160, but would be a significant upgrade.

For a better dac/amp, the fiio k3 is a good way to upgrade. There would most likely be a quality bump, but not a night and day one, but definitely enough to notice

Edit: prioritize the headphones first though

You don’t. Wanna start looking at DAC amps until you need something with power or if your DAC is facing too much noise.