I am becoming much more comfortable with the song. It is coming a lot more naturally. Unfortunately I am unable to upload the recording I made on garage band but I find the recordings I make in voice memo sound a lot better anyways.

To find out why the recordings I made on Garage Band sounded so off, I recored my roommate playing Country Road by John Denver. Although he was both strumming and singing quite loud, It still did not sounds right. The sharp noises of his guitar were picked up much more clearly then any other noises. Furthermore his voice sounded quite distant. If I was going to pursue this kind of recording further I would invest in a proper microphone.