It would be great to define dependencies between options, such as:

class_option :generate_migration, :type => :boolean
class_option :table, :type => :string :desc => 'Database table in which to operate', :depends => [:generate_migration]
class_option :add_columns, :type => :hash, :desc => 'Columns to add to table', :depends => [:table, :generate_migration]

Actually, the last example uses [:table, :generate_migration] just to illustrate, since :table itself depends already on :generate_migrations. Alternatively, :depends could also accept a symbol or string in case of a single dependency.

Additionally, an :assumes option would be also interesting. Suppose this statement:

class_option :table, :type => :string :desc => 'Database table in which to operate', :assumes => {:generate_migration => true}

In this case, passing a table option would assume generate_migration is set to true.