First, it varies and depends on which harbor, the weather and your "reason" for the call.

If you call with a question which you're inquiring about. In the "old" days the Coast Guard would answer questions and help in general situations. The "old" days are long gone. With rare situations, in an emergency (after a routine of where are you, what's your problem, do you have life vests on, how many people aboard, etc.), you're likely to get some assistance; otherwise, it will be a referral to VHF or Cell numbers for other providers you might try.

Generally a harbor master, marina, mooring field operator, and occassionally other boats are a better provider of anwers. You can get listings of these on one of the cruising gudes which are published with various listings.

I would think, that either small chart plotter and radar would make your life a lot more relaxed.

From my experience, planning ahead and picking a route which doesn't put you in tight approaches goes a long way to making things safer. You need to mindful of current affects with your Cape Dory -- you get vaired sea states (wind against current), you're subject to being set into harms way, and you have to mindful of your ability to drive out situations.

The lobster pots are going to be something that you just need to come to grips with. Forget about sailing at night anywhere except (really) offshore.

Maine is one of my favorite places. On a clear day it's heaven; but, it can become otherwise in rain, fog, and the wrong set of winds and current.