"Can I get some cruising sailors' guidance on choosing an insurance policy?"
"There is no such thing as a bad boat, just one used for the wrong purpose."
Analyzing Your Boat Needs
Computers on Board
Ports and Windows
So many skills! Sailing, Shorthanding, handling Heavy Weather, Anchoring, Docking and Mooring, Motoring, and Crewing to name some major ones.
A good cruising skipper has Piloting Skills, knows about Weather, maybe even knows Celestial Navigation. And the crew should at least be good at Watchkeeping and Log Keeping.
Are you ready to handle a Grounding and Towing situation? A Collision? Crew Overboard? A Medical Emergency. Do you know the VHF distress protocol?
Training for formal Qualifications, can be the best way to learn about sailing, mechanical systems, navigation, and other subjects. Or attend a Cruising Schools to get both instruction and sea time.