On getting the material right,

My mother lived in sheltered accommodation where they would get entertainment occasionally. Her complaint was that the singer would always pitch the songs too old.
As she put it, the Daisy Daisy brigade died years ago. Try to work out what songs were popular when they were in their teens and twenties. In my Mum's case that was the Glenn Miller era, although she would happily sing along to a Beatles medley at the age of 85.