When I was younger, think I spent a total of $5,000 on subs, amplifiers, and high end audio for autos. I'm a relatively on and off audiophile, although I've been listening to music for at least 10,000 hours in the last 2 years alone. But lately with my new job I work alot of overtime, and my work place allows me to listen to headphones, I wear them all the time.
My (IEM) journey began about 3-5 months ago when my $20 sony mdr58v earbuds broke. I thought nothing of it, and bought a more expensive earbud as an 'upgrade' but then I realized that it just couldn't compare at all to the cheap sonys. The new earbuds had barely any detail and was just bloated with fake bass, and that really really really bugged me. Several hundred $$ later, I just wasn't satisfied with anything of lesser quality than the sony mdrex58v which was ironically only $20. I then happened to find this site and thats when I realized that I was at the beginning of the road through audiophile (IEM version) land.
Although I'm relatively new (with IEMS that is), I've spent a lot of money in a short amount of time to satisfy my new hobby:
$60 Fiio e11 -- Bought it for good reviews, and it is good. Bass boost function is very nice, but kinda darkens the sound.
$30 Maximo 390 earbuds -- Very dark, bass is very weak and distorts alot.
$300 beats Studio -- Just horrible all around, I don't know how people can stand it. I am a basshead and this is not bass. I guess I just bought the brand name. Very muddy, treble don't exist, bass is bloaty and not enjoyable. I thought bigger cans = better music. Not true.
$120 SOL republic tracks HD -- Alot better and cheaper than beats, good bass but that's about it. Slightly more detailed and less veiled than beats, but again the highs are very muffled.
$70 sony ex510lp -- Beat the sony mdr58v on all fronts, except transparency. But bass was thin and distorted at high volumes. Also too sibilant.
$260 sony xba 40 -- So far sony has been the only reliable quality brand that I knew so I pulled the trigger. Pretty damn awesome, better than the Beats and Tracks HD. This is when I realized that yes, I really CAN relive my bassful youth through tiny IEM's minus the physical vibrations. But then my audiophile-ness started to pick at the flaws: the subs try to play all frequencies, veiling the mids and highs just a bit, enough to eventually annoy my audiophile soul. It is slightly echo-ey if you listen hard enough, and the subs have a volume limit before they start distorting. I thought to myself, if only it had crossovers (like my old car audio systems) so that the damn subs wouldn't try to replicate the highs....
$115 Digizoid Z02 -- I wanted more bass because some of my techno/trance didn't give the booms that my hiphop tracks gave, even with the e11 bass boost. I read that this baby gave lots of bass. It does, but it needs to be doubleamped to give good volume, volume is too low. Also, makes the music way too dark, turned the xba 40's into beats.
$1260 JH16 Pro -- I just shipped my earmolds today, I consider this my first real leap into the (IEM)audiophile world. I can't comment on quality of sound yet, but I researched for weeks deciding between this, UM merlin, UM miracles, Aurisonics as-2, UE900, 1PLUS2, Westone 4R, 1964 V6, Sure SE535. Ultimately I went with the JH16 because there was just too many good reviews + the new FP tech + I cannot resist the idea of 4 subs. I wanted soul shaking bass, without sacrificing detail and clarity. It was a really damn tough decision to make. I hope to be blown away by this when i finally get them next month.
$190 JDS labs C5 amp -- I'll need an amp to go with my jh16's (and LOD from ipod nano 7th gen), and I heard this baby is more transparent and neutral than the E11. Also I heard the bass is just as powerful, but better overall, and doesn't interfere with the other frequencies as much as the e11. Just ordered a few hours ago.
I also plan to get an aftermarket cable, still doing research on whether or not it is really worth it.
Music I listen to: hip hop 10%, Jpop 10%, Rock/metal 25%, techno/trance 30%, soundtrack 15%, others 10%