Well, just a little background;
I'm 37 y/o 8.5 year Army vet and work in a nuclear power plant. I love to ride motorcycles and whenever I'm movin, either on two or four wheels I love listening to my music. I listen to all types of music from country to rap, classic rock to hard rock and some heavy rock. I love good sound quality, I usually upgrade my vehicle sound systems ie new head unit, amps and upgraded speakers. I did the same on the motorcycle, just didn't change the head unit as it is integrated to other systems on the bike. (cb, handlebar controls, intercomm)
I often listen to the headphones while working in the yard. Now that I am getting into the bicycling world (no radio) I want to get some nice headphones. I have purchased numerous brands of universal in ear buds such as Urban Ears, Klipsch, Skull Candy, JBL, mostly the average Best Buy type stuff that you get for around the $30-$80 range. The problem I have always found is the sound is never the quality that I am looking for unless I have them crammed so tightly into my ear I end up with an earache within 30 minutes of use. I have used the different ear canal adapters but they aren't the right kind that will hold the bud in or prevent the pain. And if I am to start actually doing some serious cycling I am gonna need some that will hold up to getting a bit sweaty and stay put but not kill my ear.
Someone suggested CIEMs but I am curious, all the reviews that I have seen on this forum and online elsewhere the prices are pretty astronomical. I wouldn't mind spending $200-$400 if I were to buy some that fit perfectly and were durable and strong enough that I wouldn't need to buy another pair for a say 5-10 years. I have probably spent that much on the average Best Buy type ones over the past 10-15 years anyhow.
What I am looking for as far as sound quality is the warm sweet sound. I like the bass to punch a bit but hate when that punch kills the mids and highs that make the sound what it is. This is why I believe some 3 to 4 driver monitors would be exactly what I'm looking for in a good pair of headphones. And since either I'm a sensitive little girl or my ear canal is just not "Universal" is why I was leaning towards the Custom molded ones. I don't need studio quality sound but I am definitely looking for good quality sound that will keep me "in" the music experience, something that stays put but doesn't cause me pain. Is that too much to ask for? Am I expecting too much? Should I lower my expectations just because I want good sound from something small and light? I use supra-aural headphones on my computer and don't need something that ungainly while riding either of my two wheeled ventures or doing some yard work.
Thanks for your input and any advice is much, MUCH appreciated.