Bases on your question I believe it's safe to say that your offshore experience is somewhat limited. The only way to get practical boating experience is to actually go boating under various conditions. I'm not saying head out to the deep blue sea but you may want to fish the bay and even try inclose spots outside the pass. this way you will start to gain experience at the helm under more adverse conditions. It's also a good idea to have someone with you that has some experience at the helm, it's easier to learn from someone else than the school of man that scared the crap out of me.
Your experience and confidence levels go hand in hand. Keep in mind that your boat must be kept in a well maintained condition as well. On a poorly maintained boat, discrepancies that aren't apparent on flat seas may become life threatening under more adverse conditions.
www.ndbc.noaa.gov closest buoy to Pcola is 42012, Orange Beach buoy.Thanks again. Keep teaching I'm listening.