I've finally built a playlist to keep me running on a steady pace. I utilized an application which automatically calculates the BPM of songs in a folder, and supplemented it with a website that allows me to check the BPM manually. Using this information, I created an hour-long playlist of songs matching the 82-86 BPM pace I am comfortable running at, and will test it out on my run tonight.
My issue with storing my phone and keys when running has been resolved effectively, but unconventionally.
My new shoes arrived; after breaking them in with normal daily wear for a few days, I've started using them while running, and have noticed that my feet don't hurt nearly as much after a run as they did in my old shoes.