Josh,
Optimization is when you don't have matching darks. Lets say you have images that are 10 minute exposures and only have 15 minute darks. You are optimizing or scaling the dark to use with the shorter light exposure. At least that is my understanding. I do this with my flats. I have a master bias but my shortest darks are 300 second so by checking the optimize box I can use a longer dark. You can't do it the other way, shorter dark than light. At least this is my understanding. Personally I have a master dark library that is based on my normal exposures of 5, 10, 15, and 30 minute exposures. When I did M42 and had 30 second, 60 second, 3 minute, and 5 minute exposures, this being with a Tak FSQ-106 @f/5, I used my 10 minute master dark. I keep a seasonal library of 10, 15, and 30 minute masters which is what my exposures normally are at temperatures that range from -30 to -10 in 5 degree increments. Some just scale but I prefer to use darks matching the lights.
Hope this helps.
Steve