This Paper presents a series of empirical studies involving approx. 850 students to show howflexibility in course design should be informed by the student‘s culture and native language (L1), gender,and age, and explains how to decide on the most appropriate learning technology in course design by applying the Theory of Transactional Distance. Curves are presented to show how academic English reading ratesonline and offline are affected by the L1, gender, and age (over a wide age range 18-81 years old). Toprevent inequitable culturally-distinct overload, course design should be modified using hypertext. Choice ofmedia in particular synchronous versus asynchronous media is decided according to the Theory ofTransactional Distance. This theory is here extended from tutor-to-one-student to multiple students in agroup, and the masculinity can be modified. Briefly, at initial maximal distance ( D-S-) early on, thecommunity is fostered with synchronous media for cooperative group learning, followed by ( D-S +) collabo-rative learning using one of two frameworks presented to ensure constructivism in asynchronous mode, then(D-S+) collaborative for Guided Didactic Conversation in asynchronous mode, and finally ( D + S -) coop-eratively in synchronous mode for reflective sharing of course learning experiences. At each transactional distance, tance, or in each mode, hypertext is purposively designed to complement the cooperative or collaborative styleto provide self-access support (additional analysis and reasoning to cooperative, and examples to collaborative) to provide equitable content and quality of learning across wide cultural and L1 ranges, to remove gender bias, and to accommodate variations due to student age. Thus, to promote student autonomy and lifelong learning.