Why is caulking important?
Water that enters the end grain of siding or trim boards causes paint failure. You must do what you can to minimize and/or eliminate this kind of intrusion. I prefer the standard acrylic latex caulks for this purpose. Do NOT caulk the bottom edge of clapboard siding! These boards must be allowed to move and breathe. That small crack allows the siding to move. It can also allows water vapor to escape.