If I gain the skill level desired for sailing competently on my current 23 footer and my health doesn't fail me, I'd like to live aboard a larger boat when I stop working. I'm saving my money in a 401k that is low risk at 10% per check, with a 5% employer match. I'm not anywhere close to retirement though.
I'm thinking the sailboat live-aboard lifestyle would be awesome. I know a live-aboard fellow who is my absolute sailing guru, and I occasionally hire him to help fix things on my boat. I'm going to help him rebuild the stripped out insidesof a 30-footer he's going to buy real soon. Amazing potential there, and it caused me to dream, dream, dream.
I'm learning something new every day about boating, and I think about sailing most of my waking moments.
Edited to add: I'm very good at living cheap, if need be. I make most everything food-wise from scratch, have a few skills beyond my job, so I think I'll make it just fine living on the water, eventually.