So, I had never heard of Kaggle until reading your post--thank you so much, it looks awesome. Upon exploring their site, I found a portion that will guide you well. On the competitions page (click all competitions), you see Digit Recognizer and Facial Keypoints Detection, both of which are competitions, but are there for educational purposes, tutorials are provided (tutorial isn't available for the facial keypoints detection yet, as the competition is in its infancy. In addition to the general forums, competitions have forums also, which I imagine is very helpful.
If you're interesting in the mathematical foundations of machine learning, and are relatively new to it, may I suggest Bayesian Reasoning and Machine Learning. It's no cakewalk, but it's much friendlier than its counterparts, without a loss of rigor.
EDIT: I found the tutorials page on Kaggle, which seems to be a summary of all of their tutorials. Additionally, scikit-learn, a python library, offers a ton of descriptions/explanations of machine learning algorithms.