Small boats are harder to sail than big boats. The transition to simply sailing the big boat will be the easiest part.
The biggest surprise will be how many things break in a bigger boat and that often you need to fix them. Learn about your aux motor, and all the other comfort systems (fresh water, stove, whatever else you got). Learn about bigger boat rigging, steering, and where all the holes are in the bottom to let water in and out. Get some tools and put the aboard. Expect stuff to break. Stock some spare parts on board. Shake stuff down before you venture too far.
In terms of priority if the rig doesn't fall on your head, rudder is intact, and the boat stays water tight, the rest is just about comfort and convenience
Venture further and further as your comfort level increases. Anchor out. Learn to navigate. Learn about the weather. Learn the rules. Get some good charts.
Your approach sounds reasonable and responsible. Go down east! Sail on!