While I appreciate the sentiment, and not to drag this thread in a different direction, I was a civilian and could quit at any time. For me, it was "just" a job (though I enjoyed it, and that isn't REALLY an accurate characterization of how I felt about my work there). You and your brethren made a real commitment and are the ones who deserve our thanks.
I am certainly sentimental
As to your goals, you are in a better position than most of the "I need a bluewater liveaboard tomorrow" posters here to understand what this really entails. That being said, since you're still a novice to sailing, I would respectfully suggest that it may not be all that you think it is. I could be wrong, and you may very well understand what you're in for or at least be willing to tolerate the fact that it may very well deviate from what you're envisioning, and you don't care because you will have lived/realized the dream. In that case, I look forward to reading about your adventures! But for many, the purchase of a large boat represents a significant investment, and there are many boats out there whose owners had dreams and aspirations that were similar to yours, and then realized after jumping in with both feet that it isn't what they expected. The boats sit idle at a slip, or on the hard, deteriorating by the day as the owners try to sell the boat, their finances hanging on by a shoestring (if they are lucky). I've said it many times before here - my goal is to make sure you're going into this with your eyes open, and as informed as possible about what you're getting into. As long as that's the case, then I wish you well in your endeavor.
What is your plan for learning to sail? Will you take ASA courses, or buy a boat and learn on it?
I definitely understand. and please feel free to tell me if my eyes are bigger than my stomach, I am always biting off more than I can chew. Thank you for stating that. This is a 5 year plan, so there are a lot of things that need to come together for it to happen. You bring up an interesting question in my mind about learning to sail:
1. What is your thinking on the classes first, then buy a boat Versus Buy a boat and learn on it. I am sure there are positives and drawbacks to both. My thinking was that I would learn to sail through classes. However, as DRFerron pointed out about the Wind Works sailing club in Seattle, it seems awfully expensive to go through their courses. Taking all their courses would probably run in the thousands of dollars (basic Keel boat, coastal cruising, navigation etc.) although they are an ASA certified instruction, and clearly I need to be trained up. I don't want to take a soaking in the process.
1. What were some unpleasant surprises for you when you first started sailing?
2. What are some bits of information you would have liked to have had that you didn't get when you first started sailing.