I’m a sailing instructor and new at sailing a Nonsuch too. Going out for a motor is a fine idea for practice on docking and undocking. You might want to give yourself a wind speed threshold to try out your sail ( like 10 knots or under). There is lots of good advice about preparing to sail at the dock when you are solo. Also a good idea to be ready to anchor before you leave the dock is a good safety measure. Like others I like the power winch handle and auto pilot to raise the sail. I would mention that in raising the sail be sure the reef lines are ready to pay out as well as everyone’s recommendations on the choker and topping lift lines.
I’m in favor of an inflatable PFD but I would recommend that a waterproof VHF is attached to it or you by a lanyard. Mine has an emergency button on it that will send my location to local boats and the USCG. Some have wireless remotes for their autopilot which can be handy onboard but possibly lifesaving if you are overboard solo.