Version info:
Alfred v2.2 (243)
OSX 10.8.5
iTunes 11.1.5 (5)
Steps to reproduce:
Close iTunes Open Alfred's Mini Player Choose a song or playlist to begin playing Switch to iTunes window Note that the "Now Playing" area (not sure of the technical name; where it shows the song's progress bar) is static, like nothing's playing
Skipping to the next track, pausing/unpausing, selecting a new track in iTunes, nothing seems to fix it. Have to close iTunes and relaunch.
There's a track playing in iTunes in this screenshot: