Hey Corey, it's a little ugly, but you can do something like:
every 1.month, :at => "January 2nd at 5pm"
And it will run every month (not just January) on the 2nd day at 5pm. Whenever uses the Chronic gem to parse dates/times and it doesn't have nice way to say "the 2nd" so you have to provide a month name (which Whenever then ignores).