For me, a Best Of list is fairly easy to determine. Statistically speaking, the songs listened to the most often are a good indicator of the those that were the most prevalent in your life. Using a combination of last.fm tracking, iTunes play counts and plain ole personal preference from that pool of choices makes the whole process cut and dry.
I fully believe in the idea of music, and the experience that comes with listening to it, being entirely subjective and contextual. These songs may not be challenging the status quo of music itself (and certainly aren't picked in an attempt to showcase my non-existent cred) but their personal relevance in my life is intact.
Simply put, these songs were in heavy rotation throughout the year and represent the music that I listened to the most because it appealed to me the most. Hopefully that fits the bill of the definition of a singular persons Best Of list.