to be honest, i probably dont get 100% performance out of my m50s.
i use them mostly with my cell phone, mp3 player and laptop without any special amplifiers or dacs. if i'm at home i can use my receiver as an amp (which isnt bad) but still not as good as i could be using. i bought them because i wanted good sound which didnt need any special equipment and they work nicely for that.
i used to use ipod in-ears, sony in-ears and gummy in-ears with my phone and i can tell you for a fact that all headphones do NOT sound the same on phones. the difference is staggering. i could literally hear notes that i didnt even know where there in music i've heard hundreds of times.
if you dont like the onboard sound in phones (smartphones) you can always use a dac which can connect up to an android phone to completely bypass it. one of the fiio dac-amps is meant for android. if i cared i could probably go this route but i'm perfectly fine with the sound out on my older droid incredible 1 running miui rom.
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the m50x is a newer version with detachable cable. i've heard it might be a slight improvement but its similar. considering you can get the m50s as cheap as $99 open-box but brand new... its hard to recommend the new version unless you wanted the detatchable cable for some reason.
for the price m50s are very hard to beat in terms of quality and sound. they do sound a bit warmer toned, and dont have the depth that some larger soundstaged headphones have and they may be a bit more focused on highs and lows than mids but they are a solid choice and very good set of headphones. what i like about them is how they can hit pretty low but still sound clean and still manage to produce some clear highs at the same time as hitting hard with bass. vocals&bass such as those by evanescence are wonderful. if i ran them with a dac-amp and with flac... i'm sure it would sound a bit better but i'm not a complete audiophile.
the dt770 is a direct competitor with the m50s and boasts a bit of a wider soundstage even though its also a closed design. the m50 has more bass but the 770 is more mids centered. there are 3 versions (32, 80 and 250ohm). the 80 has the most bass (still less than the m50) while the 250 is most neutral sounding. the first two can be driven unamped normally (80 may be an issue for some devices though) but the 250 requires an amp. (a soundcard can power any if its good but for portable devices you need an amp).
the hd598 might lack bass however it has a huge soundstage and gives music and games lots of depth. as long as you arent a basshead you might like it. quite a few people who want something better than headsets use it for gaming.
the q701 is also a really nice set however its also lacking any substantial bass at all.
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there are some really nice speakers available in the mid 100's however they are 2.0 or 2.1 such as the soundsticks iii, creature iii, t40, t20... in that budget its going to be hard to get any sort of "high end" 5.1 speakers the z906 is double that. for your likely budget the z506 and similar sets are all you will find and i dont think the sound quality is up there with a good set of cans (although it certainly isnt bad for the price... remember you ARE getting 5 speakers and a sub for that money).
i would say you can get a better sounding pair of headphones than speakers if you go with a 5.1.... however if you went with 2.0/2.1 speakers its closer but i still say the headphones might be better.
as for which you prefer... that depends on what you want. if you dont like headphones on your head then go with speakers. if you want great quality at a lower price then perhaps headphones.
as for which headphones to go with... that depends on your listening preferences.
oh and i wouldnt really consider your $14 headphones too much into the equation. while i'm sure you think they sound good... the truth is that they arent even in the same league. i thought my ipod in-ears sounded nice too
you might want to keep them for now and use razer surround until you can save up money for something better though.
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ultimately the decision is yours to make with what you prefer.
if you have an audio store like guitarcenter near you then you can likely find and test out these headphones. best buy and other stores might have a few of them.
while sound is going to be distorted by whatever speakers you play them over... this listing can give you a general idea of how headphones sound in relation to one another
http/www.sonicsense.com/blog/headphone-shootouts/which-headphones-are-best-listen-here-for-yourself