Your correct on the SA and ORM, it's kept me safe so far in my current job and as for when I was in the military, I was a C student. In 2005 I became a disabled veteran, but I had a lot to think about my actions and action of others in the hospital.
I mapped out my possible sleeping and landing spots in 10NM increments along the coast. I used overlays of state parks, WMA, camping areas, national parks, wildlife refuge, etc. The State of Florida just created a paddling trail around Florida, so half of my work was stolen from them. With all that, I have about 80% "allowed sleeping spots", the other 20% is exploration and a little luck.