I agree with your pilot's sentiment of always keeping in mind the nearest bailout spots. Whenever I sail unknown waters I make such a list and keep it handy. For example, the folks on this board were very helpful in developing a list of all-weather inlets along the SE US coast when I was heading down that way. For Belize I did a lot of reading and made a list of all the harbors that were protected from Northers, which is the big weather event down there.

Once you've cruised Maine a few summers you'll have a pretty good idea of where things are and where some of the easy-access harbors are for fog, engine trouble, heavy winds or whatever. Simplest way to get up to speed might be to sit down with a few charts and ask folks who have been cruising Maine where are some of their favorite stops, and where they would bail out for bad weather or emergency. Happy to do that with you at some point. As a Navy navigator, airplane pilot, and the fact you're studying all this stuff in January tells me you are going to be further ahead of the game than you realize. But getting the local knowledge always makes things alot easier. I think Doug mentioned Active Captain, and I agree that is a really useful resource for specific harbors.

Glad you made it to the board, lots of helpful folks here!