I just found a really good summary that references some of the points made in my Day One post. It's easier to follow and I'm going to implement it step by step. Here it is: http://thepointsguy.com/beginners-guide/
Okay, so with a few easy steps, I signed up for Award Wallet (which is free and recommended by all the travel websites) and I already benefited! After registering, I immediately learned I had a $200 JetBlue credit - I didn't even know they had given me $200 for a delay on my last trip. Hooray!