Hi Nathan, I think there are quite a few good tutorials for Ruby and Ruby on Rails too, perhaps you already know some of them like

Ruby

http://pine.fm/LearnToProgram

http://rubymonk.com

http://rubykoans.com

http://rubybits2.codeschool.com/levels/1

Ruby on Rails,

http://railscasts.com

http://ruby.railstutorial.org/ruby-on-rails-tutorial-book

https://class.coursera.org/saas/lecture/preview/index #coursera saas course with ruby on rails as medium

Challenges or puzzle

https://www.hackerrank.com