Instead of using Console.WriteLine for everything, I decided that it's time to switch to a more mature logging platform. This will enable me to better track any kinds of issues, and make sure that there is an actual log file that lives outside the console that I can use for diagnostics.
Instead of relying on MemoryCache, I am using Rx, per a suggestion from Twitter, which enables me to automatically de-dupe things on the fly instead of using a polling method for a temporary cache.