I have done most of my fishing offshore and much of it in lesser boats, I don't have any doubt that your rig can handle what you are doing and more. That being said, I have learned that that little voice in my head is there for a reason. You may be able to find a local captain or mate with experience doing what you want to do in the place you want to do it and hire them to go out with you on your boat pretty cheap. This would give you a presumably safe voice of experience at your side and probably make a world of difference for your fishing success. It is a good idea to make a ditch bag with an EPIRB, handheld VHF and plenty of flares and keep it in reach. You will be surprised how quickly you get comfortable with going out on your own - just make the extra precautions a habit and keep listening to that little voice.
Tight Lines!

Thanks for all of the advice fellas. I have a friend outside of Charleston that has lots of offshore experience and I'm going to try and drag him along. Thanks again.