If your current plan is working well, and Rails is making sense to you, then fantastic. I often encourage front-end devs getting into back-end Ruby to first go through Sinatra. Building a very simple tool (shopping list, address book, etc.) in Sinatra and then replicating it in Rails will give you a good sense of how they're alike and how they're different. And because Sinatra is so much less "black box-y", you'll have a better sense of how the code is working.
Thanks for the tip. I often get wrapped-up in the buzzwords then end up splitting my attention between a million different areas that I forget to build up the basics or start small. Sinatra looks like a good gateway to understanding the 'magic' behind Rails.
Ask HN would have been a much better place for this post. I hadn't realized that if you include a link, hn automatically directs you there. I'll re-post in Ask so comments are easier to make.