What's it all about?
Okay, so we all like to play guitar, but why? I used to enjoy the personal challenge of being able to play music and everything it involved - learning new skills, memorising songs, developing the speed and dexterity to play a tune accurately. The satisfaction of hearing a song come out from a guitar in my hands. Eventually that wasn't enough, I wanted other people to hear it. Pride and ego? I don't really think so, it's more of a case if you owned the entire world but didn't have anyone to share it with, would that be satisfying?
Playing for an audience...there are two ways of doing that I can see - play what you want to play and hope that there is an audience to suit you...or play what you think an audience wants.
Having been reasonably well accepted on youtube I have a perhaps overinflated expectation of what listeners think of me. Out of say a billion people who have had the oppurtunity to look at any of my work, there has been about a million and a half who _have_ looked...which means just over one person in 1000. In two and a half years of being there. Now if you were sitting on the street playing for random people, 1 in 1000 equates to, well, almost nobody.
To lift the odds I have decided to play more for an expected audience. I've approached that by examining what my most popular videos are, and examining the most popular videos of other players. Naudo is an excellent indicator because (a) he is an unknown - that is, nobody is searching for his videos unlike say Tommy Emmanuel; (b) he has a lot of videos of covers to form some good popularity statistics.
Oh, I probably should mention that playing for an expected audience means playing stuff that they will know. People like to hear stuff they already like. If you were a big popular artist then you can play original stuff, but the guy playing original stuff on the corner needs to be either stupendously engaging, or playing on a corner that a high number of passers by are into his form of art. Open mike is probably a good scenario, otherwise both cases are otherwise unlikely.
Another part of the puzzle is you probably need to be able to sing. This is a double edged sword. If you can sing and play guitar you will attract far more listeners in my humble opinion; but singing is a land of personal taste and has a lot of room for error. For example, when playing the guitar most people won't notice the odd non-fatal stuff up, but stuff up singing and people recognise it in a heartbeat. Then there is whether the audience likes your voice - the personal taste thing. You do kinda need to be a good singer.
To avoid singing you unfortunatley need to be able to play the guitar really well, dare I say fingerstyle covers - catch a whole song on one instrument. I recommend learning to play simple guitar and developing your voice ;) Oh, if you are a good-looking girl then that helps immensely...
I'm not sure if there was a point to all this, lets see if I can summarise:
(a) Eventually you will need to play to an audience;
(b) Play stuff that people know;
(c) If you can't play oustanding fingerstyle covers of stuff that people know, then concentrate on your singing.
I promise I will reassess these statements when I start playing to an audience :)