Particularly when dealing with a rough wood exterior, mold can be a problem. If water has gotten into the crevices of your wood, there may be some mold already starting to grow. If you paint over this mold without tending to it first, your paint job may suffer as the mold can continue to grow and ultimately cause chipping. To insure that mold isn't lingering in these cracks, use bleach to clean the surface, scrubbing it down with a mixture of one part bleach to one part water, then allowing it to dry completely before you start your painting project.
Because the surface you intend to paint is rough, standard painting supplies simply won't do. Instead of using the old classics, purchase a heavy nap roller for textured surfaces. The use of this roller will make getting into the crevices in the wood much easier, ensuring that you get the full coverage you seek. When buying paintbrushes, don't skimp, as a cheap brush will likely lose its bristles on this rough surface, leaving you with a finish that is not as smooth as you may have liked.
Particularly if this is your first time painting this rough cut wood, priming is a must. If you attempt to skip the priming step, you will likely use more paint, as the wood will absorb it, and you may also fail to achieve a finish that is as clean as you would like. Purchase a primer specifically for use on wood and exterior surfaces to ensure that you have the right tool for the job.
Whenever you paint wood, and particularly when you paint rough wood, you must go with the grain. Run your brush or your roller back and forth in the direction of this grain, allowing your paint to deposit itself naturally in these wood groves and creating an attractive finished product.