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I'm 16 right now and I've been considering custom IEMs for a while now, however I am afraid I might have to get a refit/remold every year or so. Does anyone have experience or have knowledge with ear growth, IEM fit, etc.?
You're in Southern California, according to your location information. One of the posters recommended asking an audiologist and another pointed out that none in his area had even heard of custom IEMs. I'm 51 and own lots of headphones and IEMs, including a custom job that some consider the best currently made. I'll try to give you some advice and you can take or leave it as you wish.
First, the poster who recommended asking an audiologist is absolutely correct.
Second, the poster who pointed out that many audiologists don't even know what an IEM is, is also correct.
Third, therefore, you need to find an audiologist who knows about IEMs. Because you're in Southern California, you should have all the resources you need locally.
Fourth, go to the websites of one or two of the major IEM makers and look up audiologists in your area who they recommend as having experience with custom moldings and IEMs. They should know the issues about the use of IEMs by young people. There are others, but two top companies in the IEM field are JH Audio and Westone. I own the JH-16 Pro. It fits me like a glove in each ear, which are different from each other in structure as is obvious by looking at the finished product. My right ear canal takes a sharp turn upward while my left canal is practically straight. Now I know why the left earpiece of off the shelf models often fell out and the right earpiece had trouble staying in. With my JH, both fit perfectly and I can wear them for hours without fatigue.
Fifth, it should cost between $50-$200 to get the fitting, depending on location and audiologist. The actual fitting takes just a few minutes but you only get one mold and you have to send it to the company. You don't get it back after your unit is made in case there is any trouble with your fit (very unlikely - these companies know what they're doing).
Sixth, young ears are especially sensitive to damage from IEMs. Custom IEMs lock in the music and have many drivers, including good bass drivers (mine has 16 drivers for each ear). That may "sound" good now but, if you're not careful, you can cause permanent hearing damage. I'm not telling you this to ruin your party. Deafness runs in my family. When I was growing up, I remember many of my father's relatives always yelling at each other. They were all hard of hearing. That was congenital but whether your hearing loss is congenital or environmental, it amounts to the same thing. Losing your hearing really sucks.
Seventh, if you're intending to use the IEMs while exercising or otherwise engaged in athletics, study the issues first. There's growing evidence that whatever hearing damage IEMs do to young ears (adult ears, too), is made worse when used during strenuous activities. But it always seems to be more dangerous for young people versus older people, though. I don't know why this is but I've read it in sources that I think are reliable.
Eighth, the best IEMs, in the opinion of a middle-aged guy who owns top IEMs, top headphones and fine speakers (not the best of the best $50-100K+ but still "reference quality"), is that the best IEMs are not as good as the best full-sized headphones in sound reproduction, which are themselves a totally different experience versus fine speakers (not necessarily better or worse but definitely different). As good as my JH-16 Pro is, and most people would rank it among the very top of the top, I don't consider it, for my tastes, anywhere near the sound experience of my Audeze LCD2 or other comparable headphones. In other words, the best IEMs, if you decide to go that route, are lots of money and you might consider instead a full-sized headphone, which could cost about the same and give you more enjoyment. Also, if you find out that your ears are changing, that will never be an issue with a full-sized headphone so long as your head never becomes too big (literally and figuratively). As with all other opinions, YMMV.
Ninth, if you decide to go the off-the-shelf route, consider the Shure SE535. Many consider it at the top of the non-custom heap. I have one and think it's great sounding (for an IEM). Unfortunately, because of the shape of my ear canals, I find it uncomfortable to wear for long periods. Most people don't have that problem. Sound quality is tops and it costs about 1/2 or less as much as the best from Westone (ES5) or JH Audio (JH-16 Pro). Klipsch makes a couple of fine off-the-shelf units too. One is the X10 (their top of the line) and another is the S5 (very good value). Klipsch also has a "ruggedized" S5 if you expect to treat it roughly. Add an "i" to the model number of these Klipsch IEMs and you have a unit with a volume, repeat and skip control in the wire for your Apple iwhatever.
Tenth, that's it. Good luck and I hope you have many years of music enjoyment. Enjoying good music is one of the finest things you can do in life until the very end (so long as you don't become deaf).