This is the best answer I can give. After 8 years of owning a high end shop, I can only remember about one convert per year and that was long before MP3, I Pod and other portable mediums.
For the most part high end or quality systems just do not appeal to the masses. Today I feel it is much tougher to open the door to the uninformed. When I Pod and MP3 offers the total ease of music reproduction,albeit the sonics are just dreadful to say the least. High end audio for all its prowess in the last 30 years has yet to expand beyond its core group of customers and that base is shrinking each year as this group ages.
While music remains important in peoples lives, its the delivery of the music that has dramatically changed and continues to influence the newbies. They cannot justify the expenditure, time and effort audiophiles put into systems, when they have other delivery methods, that appeal to them at far lower costs.
The only convert I have had of late occured about 4 years ago while I was in the Denver,area. A gentleman and his grandson visited my home as he wanted to purchase some vintage gear that I had. At the time had four systems up and running. As we were discussing, the college student was listening to his MP3 player through headphones. As I was demonstrating the systems, his eye caught hold of a turntable, thats when he got involved. He had only heard about these and never heard one. So I showed him how to use the turntable and the system and pretty much left him to his own devices. The system was a Classe DR8 power amp.,Classe DR5 preamp, Denon 1560 CD Player,Denon DP61F turntable pushing some original Quad 57 speakers.Showed him where the CD Discs were and the LPs. Told him knock hinself out. High end yes, but a little long in the tooth. Continued showing the other systems to his Grandfather, who ended up buying a good deal of equipment.
At the end of the day found out that the Grandson was a music major at U of C. He thanked me for letting him use the Classe system and that the sound was all he could ask for. He really enjoyed being able to use a turntable and all. So with that they left. I had some cash and Grandad had some very nice gear. Grandad did not buy what his Grandson listening to. He bought an Acoustat system.
About two weeks later the Grandson shows up at the front door and says remember me? I got some money and want to buy a few things from you. And with that the music major was getting into high end audio. And over the course of the following year he got into it in a big way. But his friends never did.
I believe that everyone has to find their own way into high end audio and I further believe if I had tried to sell or demo something to him, it would have turned him off. But by letting him find his way on his own, he found the pleasures of owning a high resolution system.
Perhaps this is not the precise response to this thread, but is offered as my last experience with a young newbie.