Shipping with or without insurance?

I'm getting this really expensive figure with a proxy in Japan that I trust. I've dealt with them multiple times on expensive figures, but not as expensive as this. So I have a few worries.

First of, I never got any inssurance for any of the figures before and I know the my border will hit me hard with import fees on this.

Second thing is I might ship it through boat instead of air to save shipping cost. But it would take multiple months to arrive so I'm worried about damage and theft.

Do you have any recommendations on how I should proceed?