To Equalize or Not to Equalize

This is probably not a helpful answer but my old ears have a natural high frequency roll off. You could just burn in your ears so to speak and then You high frequencies will be tamed. I used to EQ but now I don’t.  I enjoy using a EQ when I had one installed so I say why not. As to which one to get I have no advice as I haven’t tried any in a long time.

The scary thing is that I have been burning in my ears for over 50 years, since I was a teen.  A good part of that span was using headphones the majority of the time.  So I'm sure, like you, my ears roll off the highs and still I find them a little harsh sometimes when I crank the volume knob a bit. 

I have a vintage Kenwood P/GEQ.  I use it exclusively for needle drops, where a slight boost in the bottom end compensates for bass rolloff in the cartridge, or bass-shy recordings.  A few dBs max.  Even though my rig is not a super hi end one, I rarely feel like I need EQ to listen.  If I do, my pre has bass and treble controls, and Roon has a sophisticated digital EQ program.  When done in the digital domain, EQ does not introduce phase shift.

FWIW EQ/DSP is an increasingly common feature in a variety of streaming applications.  

+1, @rbrannen   couldn’t agree more!