HF roll-off is part of aging too, so don't be freaked out when you're 40 and 20k no longer exists for you. It's natural. If you're 12 and this is the scenario, and there's no good medical reason for it, maybe turn stuff down.
Generally speaking, you shouldn't listen to anything at a level that causes you headaches, ringing, or any sort of pressure/discomfort. 85 dB is pretty loud just for reference (and sustained exposure does lead to fatigue) - 50-70 dB is probably where you're going to be comfortable for long-term sessions.
The argument about "blocking" (literature usually rips on earbuds not open-backs, but same principle) is very valid, and it's considered to be one of the leading causes of NIHL. I'd equate it to self-harm along the same lines as drinking oneself to death; you're actively choosing to do something that has serious and long-term consequences. I absolutely cringe when I see a young kid on a train with earbuds or even worse, closed-back ANC headphones, cranked up so loud that you can hear them at the other end of the car.
The other issue is cranking stuff up to hear one part of the spectrum because whatever you're listening through is rubbish. For example, if you have iBuds and want a lot of bass, you have to crank them up absurdly loud to get any meaningful response on the low-end. That's a problem. Instead, get something that can reach down low with a higher impulse response than the midrange (we perceive low and high notes less intensely).
As far as the amp for "extra power" - there's a perpetual belief that somehow having a mountain of power "in reserve" will improve sound quality. In other words, if I need 1 mW (which is a whole lot for most headphones), having an amplifier that can provide 5 mW is not sufficient, but having one that can provide 5000 mW is going to make some superlative difference. I'm still only using 1mW though. I also agree with the other four reasons provided.