Philip, I think this can be done very tastefully. Lennon and McCartney were masters at trading off on Lead vocals. McCartney taking sections of a song where Lennon couldn't hit some of the higher notes, and vice versa. A Day In The Life, excellent use of blending two different songs into one.
I think the thing that holds it together for me is each vocalist having the same consistent part, so that you anticipate who is singing next.