What kind of pain is your saddle causing? You shouldn't feel any pain anywhere but your butt and that should be minimal and based around your sit bones.

As far as how much to ride - I like to ride every day. Weather and life don't always allow me to do that. Realistically, I get out 3 - 4 times after work during the week on my single and usually get in a long ride on the tandem on the weekend.

Sounds to me like you're getting past the beginner stage.

Veronica