Providing meaningful telescope observing experiences for students who are deeply urban or distantly rural place-bound--or even daylight time-bound--has consistently presented a formidable challenge for astronomy educators. For nearly 2 decades, the Internet has promised unfettered access for large numbers of students to conduct remote telescope observing, but it has only been in recent years that the technology has become readily available. Now that this once fanciful possibility is becoming a reality, astronomy education researchers need a guiding theory on which to develop learning experiences. As one departure point, we propose a potential learning progression anchored on one end with recognizing that stars visible at night have describable locations and predictable motions, and anchored at the other with distant robotic telescopes can be programmed to record specific astronomical data for later analysis.