Hi Sue,
You only need more flour if you feel the dough is too sticky to roll out nicely. I don't bother chilling the dough but some people say you should for at least an hour. I just work in a little extra flour by hand when I roll it out and dust my rolling pin with flour. I don't think I have ever made a single batch but I'm guessing it would make about 4 dozen cookies depending on how big your cookie cutter is. Peggy