The maths
The chair picks from the top cycle
With more options the chair puts them in a queue: the first two face off, the winner meets the next one, and so on to the end. Tap an option in the diagram and the page will find a queue that makes it win, or tell you there is none.
The options that can be made to win are exactly those in the "top cycle": the smallest group whose every member beats everyone outside it. If there is a Condorcet winner, the group is just that one option. In a simulation with 1001 voters and random lists, there is no Condorcet winner in about 17.5% of elections with 4 options, 25% with 5, 31% with 6 and 49% with 10.
When the options form a continuum in several dimensions, say a tax and a budget at once, and there is no Condorcet winner, Richard McKelvey proved more in 1976: with a chain of honest majority votes the chair can lead an assembly from any option to any other.