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I just bought an electronic drumkit and it works great when playing it through a drum kit amplifier. But the volume is too soft when I try playing them through headphones (I know it's not the headphones as I tested with two pairs of headphones).
My question is: Will getting a headphone amplifier help to boost the volume and fix this problem?
Probably, yes. "Headphone power" depends basically on two things, output voltage and headphone impedance (I discussed it in some detail here). Many devices don't bother providing a very great voltage, but for dedicated headphone amps it's pretty much expected that they can make any off-the-shelf headphones loud enough for all typical use cases.
Still, if both pairs of phones you tested are very quiet, they likely have both rather high impedance, so you may still want to try a lower-impedance pair. Or one with better isolation, so it doesn't even need to be as loud: when you're already playing an electric kit, one of the main benefits would be squandered if you then made the phones so loud that the ears suffer just as much as with an acoustic kit!
There's no rule for that. If the designer decided that the headphone amplifier should have some gain, it'll have some gain. A good clue would be does it have a volume control. Usually when someone puts in a volume control he makes it so it goes up as well as down. Such is the case with my old MXR headphone amp.
But really you have to ask about the box you're looking at. Pick one that you think you like and find someone on HeadFi who owns one and ask him.
Postscript: I just bumped into this while doing something else: http://classicalmusicheadphones.reviews/headphone-amp-buying-guide/ It might be useful to you.
