How to Get the Most Out of a CDN?

The idea was take a whole bunch of traffic and load off of my servers and put it on CDNs. It would be faster and you download faster to everyone's devices, especially people who don't live near Texas. And the times that it has worked less well, were mostly because I was trying to add levels of caching which ended up resulting in possible failures in bugs. So anyway, there's an overcast using Blackbird by the way; nothing else yet but what you're telling me is production ready.