Back when I was in high school and college, I played the guitar and sang backup for my band. We called ourselves "Ego," and described ourselves as a "jazz-rock" band. There were eight of us, including a brass section--this splits the take rather painfully--but it was intensely satisfying for 18 and 19-year-olds to earn paychecks playing tunes by Chicago and Blood Sweat and Tears. I only sang a couple songs lead—I hid behind two incredibly talented singers who did most of the vocal work. The attached photo is Ego performing back in 1974. 
Since then, we've all gone on to pursue careers as such things as an engineer, teacher, letter carrier and lawyer (though our percussionist/lead singer, Charles Glenn, continues to make a living as a singer in the St. Louis area).
Fast forward to 2009. I would love to play music with other musicians again, but I have a day job and a family (and a blog). It would be extremely difficult to arrange for rehearsals that didn't interfere with my many other obligations. I've recently started picking up my guitar to play and sing. It’s not sounding all that bad, and I’m starting to consider performing for others again. [BTW--I had a scary episode where my left hand became numb cause by a pinched nerve in my neck. After surgery, the feeling in my hand is returning nicely, which probably explains my renewed interest in playing music again.]
I've never thought of myself as a singer, but I thought that I would have a much better chance of getting a solo gig if I learned to sing rather than just playing the guitar. Therefore, I recently took a singing lesson from Leslie Sanazaro, from whom I learned that my breathing was all wrong, a condition that can reportedly be remedied by doing exercises that would look and sound rather silly to anyone other than a singing teacher.
Leslie advised me that my pitch is okay but that I need to get out there and get some confidence. She said that the best way to get confidence is to go out and sing in public, over and over. That's easy to say, of course. If you are not enamored with your voice, though, it is a daunting task. It brings back memories when, in the second grade, every student was required to stand up in front of the class and sing a song (my voice trembled and my knees knocked as I sang “Ooey Gooey Was a Worm"). And even when I can sing a couple short songs that sound half-decent, I've noticed that in extended sessions, my voice grates on me. The fears that I'm experiencing are common, according to Leslie. She sent me this caveat by email: "Don't get too burned out on your own voice, it's the only one there is!"
My quest is thus to go out with a guitar and sing songs. It's something that I intend to do within the next month or two at an open mic session at a local bar or coffee shop. Not a big deal, perhaps. But my voice and my guitar make for such a tiny band, nothing like that eight-piece jazz rock ensemble that I surrounded myself with when I was a young musician. Are there other ways to spruce up my little band without collaborating with other musicians? Yes, indeed, there are many reasonably-priced options, but these options raise issues about the authenticity of one's "live" performance.
For purists, there is no substitute for an acoustic guitar and an un-amplified voice. That's how I often practice at home. Over the years, however, various devices have been offered to musicians which make performances less pure, acoustically speaking. We are all now familiar with electronic amplifiers for voices and guitars. Those of us who like the acoustic sound can amplify it by sticking high-tech pickups into our acoustic guitars. I use a Fishman brand "Blend" pickup in my guitar, which combines a piezo microphone with a tiny acoustic microphone, giving you impressive control over the sound. Even when it is amplified substantially, the guitar still sounds "acoustic."
So what else can you do to enhance the sound of a guitarist/singer?
