We have nine months navigation (Dec - Feb are not insured w/o a rider).
If you venture out of the Chesapeake Bay, there's a rider to go north which is relatively minor in the domestic US. If you go out of the Chesapeake Bay and South, it's a lot more expensive -- expecially depending on the time.
In 30 years, I've never been asked how often we were on the boat.
IF we were in Florida, or had year around navigation, or were venturing offshore -- then there are a lot of questions about your experience, etc.
We use Jack Martin Insurance out of Annapolis (and have for over thirty years). Julie Humble handles our account and is experienced and easy to deal with: (443) 433-5760.
If you are 3 years away from really journeying out into the great blue, I'd start with a more conventional package.