Take as many official sailing courses and safety courses as you can. Insurance companies like that. A later model 34ft sloop should be among the easier to insure and not out of reach for a newer sailor. A very old boat, particularly a fixer upper, is very difficult.
Location also impacts the insurability. Higher crime areas are naturally going to be harder to insure. More common is high rates if you remain in the Caribbean during hurricane season, where rates can sky rocket, if attainable at all. Some insurance companies want proof that you have access to being hauled in the event of a named storm. You probably want to know too.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.