I know some parishioners have mentioned the idea of streaming our Masses online, and I have said, "no". A few have asked about the idea of me recording my homilies so that others can hear them, and, yes, I said "no" to that as well. I will admit that I am a bit technophobic, but after much time and prayer, and a lot of self-examination and critical consideration, I have come to the conclusion: my technophobia has nothing to do with my saying "no". Let me explain briefly.
You have to be there. It is really that simple. Presence is a big deal in the Catholic Church. A few things can be done by proxy, but only a few. Some things require physical presence for it to count. The homily is one, and Mass is the bigger one. The homily is not just a transaction of information, it is explanation of the Scriptures in the daily readings in the context of the Mass and its proper prayers appointed for the day.
Yes, someone can tell another person about what I said, and there is nothing wrong with that. Yet, the specific experience of a homily requires that one be there for the whole thing, including the mannerisms of the one giving the homily and the entire experience of the spiritual movement of the Mass. The homily is not an isolated event in the Mass that can be picked out and dropped into another context (or at least it should not be). This means that you may "hear" something in the Mass that others would not necessarily "hear" in the same way merely by listening to a recording of that Mass. As I said, you have to be there.
So, I am honored when I hear that someone wants another person to hear one of my homilies. But there is more to a homily than the words. The experience someone has in the Mass, is not going to be the same experience, and therefore will not illicit the same understanding in the listener at a later time. Just like the Mass cannot be experienced on t.v. (contrary to the opinion of many confused people today), but will only give a person an idea of certain superficial things about the Mass. So also a the words of the homily are not the same as the experience of the homily.