How Many Choices can One Handle?

The basic problem revolves around the number of choices we have in life. Should they be limited, grouped together, or doled out one by one? Should they be free-form and open ended? This is my design dilemma. What if I get three 'T's , two 'L's and a blank? What if the caller doesn't know which options they're entitled to?

So many questions......And it's not even my turn yet.

The pressure to develop these dynamic menu choices, and construct a word that garners more than Catherine's 30 average score is ferocious.