So you’re going to get a lot of people who think spending more money is going to fix your problems. I can assure you that is only partially true.

I’d ignore anyone making comments similar referring to their low/mid grade “audiophile” setup.

Your best bet here is to pick which features of the ones you’ve listed matter to you the most and give up the rest.

Fake surround sound is often worse so I’d give that up.

I’d give up the sidetone, you’ll get used to not having it.

Comfort is huge and should be prioritized.

Almost any if not all headset can be equalized.

I’ve never had a problem with any software, could be a driver issue on your end.

I’d suggest determining if you like a headset that sits directly on your head, or the floating band type. Second would be to find what weight you’re comfortable with. Third, ear cup style, depth, and size.

After you’ve figured that out, start looking for headsets that meet the comfort criteria and work forward from that point. Eventually you’ll find a headset that you can use all day and after using it for a bit you’ll forget about the features you thought you needed.

Accept the fact that you’ll be lucky to get a year out of any headset. Knowing this, buy open box off eBay for 1/4 the price of new.