He was a minister at Adelong, Yass, Newtown and Newcastle before his appointment to York Street, the colony's leading Methodist church, in 1883.
[1] Osborne's liberal approach to religion and lack of sectarianism achieved the desired effect of increasing church attendance, but it also alienated conservatives.
Osborne did not follow this directive, and instead attended the Requiem Mass for Vaughan and supported George Higinbotham and the Australian Church radical Charles Strong.
He contested a by-election for the Legislative Assembly seat of Argyle in 1885 as a supporter of Alexander Stuart, and was only narrowly defeated by Sir Henry Parkes.
He joined the staff of the Sydney Morning Herald in 1886 but by 1889 was working for the protectionist Australian Star, becoming its editor the following year.