Great Post Michael,
I took a similar route, but in reverse. I sailed recreationally for many years, while doing the suit and tie routine. Knowing that I would retire early, and still want to be productive, I went through all the ASA instructor qualification clinics and I'm now on my second 100 ton masters license.
I will say, that while I felt myself to be a competent sailor/boater, when I began the ASA instructor Quals, and USCG process; I have learned more in the last 8 years than I did in the 1st 30.
As with most knowledge; the more we know, the more we realize what we don't know.
The internet has opened up yet another dimension of information sharing that was unavailable when I was learning. Sites like this and others allow real life experiences and knowledge to be shared at the speed of light. I've mined these sites for a few years now. The wealth of information here can't be found in magazines.