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Headphones VS. Speakers
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Before anything else, on your quest for the best sound, you must come to grips with the quality of your recordings, and remove and replace low bit rate (highly compressed and therefore very degraded) mp3's with high bit rate quality audio files, or better yet, lossless files. ALAC (Apple Lossless Audio Codec) is ideal if you like to listen on an iphone and use itunes. But honestly it is very hard (for me to hear) much difference between ALAC and a 320kbps mp3. Just make sure that your files are at least 256kbps bit rate, and ripped directly from a CD, (or the current 256kbps AAC mp4 format download from itunes) and you will be ok to proceed with buying better gear. If you try to listen to lower quality recordings, you will be wasting your money buying better audio gear. Get rid of them.
After that you will need a high quality DAC to get the most out of your high quality recordings, (even if you buy great headphones, that alone won't get you there.) The cheap DAC's in most computers won't compare at all to the quality of even a very affordable outboard DAC, such as the Fii0 E10K ($70). But do yourself a favor and just get an Apogee Groove and be done with it. The Groove is an AMAZING portable DAC that will drive 600ohm cans (if you feel the need for those things) and is about the size of a pack of gum, runs off usb power on both windows or a mac.
For utility purposes it makes sense to have a few kinds of headphones:
A pair of EIM's (in ear monitors) to plug straight into your phone for when you are on the go, and want total isolation from the outside world without having a giant goofy pair of cans on your head in public. (unless you want that kind of attention, in that case get a big bright colored pair of Beats to let the world know you care about sound)
After that it makes sense to have a great pair of circumaural (that is, around and over your ears, not resting on directly on them) OPEN-BACKED headphones that are comfortable on your head for hours and hours, but will also allow you hear what is going on around you. (to hear and get the door bell for example, or to hear people talking to you. But just remember that other people can also hear your music if you have the volume up with open backed headphones)
Next, a really good pair CLOSED-BACKED circumaural headphones that are comfortable for hours on end and won't make your ears feel hot, but with more isolation for when you don't want to hear your surroundings, or have other people hear your music (or more importantly when recording, will not bleed sound (as will open-backed headphones) into a nearby condenser mic while you are recording your acoustic guitar for example).
If you record, and have people over to make music, it is good to have a few pairs of closed back tracking headphones for them to use.
IEM: JH Audio JH-16pro IEMs - for on the go listening straight from my iphone.
Open-Backed Headphones: AKG K7xx/K702 - The most comfortable headphones ever made IMO, that also allow me hear what is going on around me.
Close-Backed Headphones: Shure SRH 1540 - The best sounding closed back headphones I have ever heard and more importantly, are SUPER comfortable all day long and don't get hot on your ears. (think hours of tweeking and mixing tracks)
Tracking Headphones: Audio Technica ATH-M50x - two pairs for tracking/recording with other people. Also they are excellent all-around headphones. If you want just one pair of reasonably priced awesome sounding headphones, these are the ones to get. (they are not circumaural, and will get warm on your ears after a while)
DAC: Apogee Groove from a Macbook Pro to get the best from your high quality audio files.
Finally, an audio interface if you want to record (or convert and digitally preserve your vinyl collection forever). Focusrite 2i4 ($200) is perfect for starters, runs totally from USB power, and will give you a mobile recording rig that will fit in a backpack. (Or get a UA Apollo if you decide you want to jump in the deep end)
If you want to listen to LP's, I would first clean them with wood glue, and then play them on a high quality turntable with a brand new stylus, into your audio interface, connected with balanced XLR cables out to powered studio monitors such as JBL LSR 305 or 308. That will give you amazing sound. Or just use good headphones instead of monitors. Record your LPs right after cleaning them, using a program such as Audacity (free), and then convert the resulting wav file to ALAC or high bit rate audio format of your choice in iTunes. After that listen to your recordings and leave your LP's freshly cleaned in (new) protective sleeves.
I really have no use for tubes, outside of my guitar amp or the one tube mic that I own. If you get a UA Apollo, you will have access to a vast arsenal of every kind of tube voodoo that has ever been made. Want warmer tube-ier sound? Slap a Fairchild or a Neve 1073 on it. That will warm it up. Lol (but most likely that stuff was already used making the record in the first place)
Not that you wanted to know all that. But there you go.