Thanks again for all the replies! I agree with MarkofSeaLife, this has been a wonderfully interesting thread.
Just to be clear on my original post though, while I am indeed nervous about the docking an general sailing execution, I'm not as concerned with the gaining of experience in that manner. I've had a few foolish hobbies during my time on this little rock, so I understand those notions.
What has bothered me the most was questioning the rigging and general gear failure and things of that nature. That part is new to me. I haven't had to rely on mechanic components for safety so much before in a hobby like this. Yes, yes, I know cars and the like... but that aside...
Since you are an engineer - do some calculations. Its easy stuff, statics. Find out what the working load is on the shrouds. Calculate what the force is heeling the boat. I bet you find out that its very low stress. During relatively smooth action as the rig loads and unloads the boat,its just like weights spinning around an axis.
The scary time would be if the rig started pumping and if that happens, you must take down a sail , or reef.
But if that is not happening,if the rig is loading up smoothly and the rudder is responding well then you are seeing clear evidence that all is well and the boat is working as designed. I am not scared when I feel the boat working well.That is a clear reality.
You also should develop a set of skills, like reefing and simply know what course to take which will allow you to lower, or more accurately, manage the stress on the boat. So you will have an ability to control the stress. I think as an engineer this will resonate with you. You know the boat can take a large force, but you subject it to less force, and you have all that safety factor. Soon, you probably won't care anymore because the boat has a big factor of safety in the rigging and combined with good management, it will out last you. Finally, we all eventually learn that the boats can take way more than we can. This is what they were built to do.