All that can presently (May 2024) be gleaned about
Rose Winchester from sheet music covers and by Internet searching is that she was presumably an American actress/singer who has been featured on 2 works published between 1895 and 1896.
Her portrait on the left is taken from
If I Only Could Blot Out the Past - Song (1896) words & music by
Gussie Lord Davis, and published by
Hamilton S. Gordon, New York, USA.
Surfers are welcome to contribute any further information about this performer.