He spent the last two years of his high school education in southern Germany (the Black Forest area), where he was prolific in his songwriting and performing.
He was diagnosed with a Glioblastoma Multiforme IV (GBM 4) brain tumor that was to have killed him in six months.
He toured and performed for a few years in the duo Not by Chance, along with guitarist, vocalist and songwriter Douglas Ebert.
On October 2, 2010, Bailey died of brain cancer following a month-long surge during which he was able to visit with family and friends from across the United States.
He attended the New Wilmington Mission Conference off and on for his entire life and was an Elder in the Presbyterian Church (USA).