I think the simple question is how confident are you in your ability as a captain. And is it worth it to have the peace of mind knowing you'd at most be out $2500 if there was an issue?

For us as owners we were going 3 times a year so the added insurance costs added up and multiple trips with no issues would easily have covered a single trip with an issue. And we had over a dozen trips and never had an issue.

End of the day, only you can answer your #1 question.