Hi Brett, thanks for sharing your challenges with enabling e-Learning access for your users, your frustration is understandable. Our team continues to explore options to solve this--it's a tough nut to crack given the security issues.
Regarding the ArcGIS account sign-in, in addition to its use as a maintenance status check, an account is the mechanism that allows us to track learner progress (and make it easy for learners to pick up where they left off), award certificates of completion, offer wish-list and learning plan features, maintain Esri training history over time, and much more. People taking free training appreciate the benefits just as much as those taking paid or maintenance-only training. 🙂 It's not likely we'll do away with the sign-in. Nonetheless, I'll pass your suggestions along.