In Sid Meier's Pirates! it was the objectively correct choice 99% of the time. Even a tiny ship could take out a ship of the line with a few well-placed chain shot barrages, and ships would pretty much always surrender the instant they lost their mast.

I think the story battles were an exception to the instant surrender rule, but without their sails you could switch to grape shot and pepper their helpless vessel until they had no crew left, then board for an instant victory.

I miss that game. I should redownload it and see how it holds up.