We hired Annapolis School of Seamanship several years ago when we bought Kismet. Being new to trawlers and larger boats, we needed to have a few days supervision to appease the insurance company. Athough I had a lot of time on the water, a 52 ton boat was quite a step up for me!
Conversely, the Admiral had no boating experience.
A.S.S. ( John Martino) coordinated to have two licensed captains aboard for about 4 days. Both were terrific and excellent instructors. They worked closely with my wife on basic seamanship skills (rules of the road, line handling, knots, navigation, radio procedures, etc), while I spent most of my time behind the wheel, docking, anchoring, brushing up on radar usage, system checks/procedures, etc.
Although it wasn't inexpensive, I consider it one of the better investments we've made. It really forced us to fast track the learning curve that we wold have otherwise stumbled through over the course of several weeks/months.
I'd highly recommend you continue down this path.