Flying magazine recently had a feature about single pilot jets, and quoted several insurance agents. It was a common theme that owners went in thinking that since the jet was easier to fly than the baron, it was a given. When the underwriter declined to quote, and the agent recommended a transition airplane like a C-90, the suggestion usually fell on deaf ears.
It all depends on experience. According to one of the agents, there is a slim chance, but there is no hope if the candidate protests and refuses a transition plan. The plan may include a simulator based ground and flight school, a type rating, followed by 50, 100, or even 200 hours of dual time with a captian qualified pilot.