I am far more lazy with my music on OS X than you are, I typically just select an album from the "Recently Added" and listen to it all the way through–I prefer listening to whole albums. If I need to quickly pick a song, I use Alfred's built in mini-player which is approximately 10x faster than going through iTunes itself. On iOS, I do things a bit differently. I use and enjoy the app "Workflow," and I made a personal workflow that when launched creates a playlist of 30 songs that I haven't listened to in the past month. This is useful due to my overwhelmingly large library (upwards of 6,000, though that has been sized down from 10,000).