I came across this point when trying to decide which Anime to put on top of my top 10 list, since I was having the problem of deciding between the Tatami Galaxy (which is incredibly well-written and intelligent and has one of the best plots in Anime ever, and I would call "the best Anime I have seen") and the Monogatari series (which I have grown quite attached to, has some of my favorite characters and moments and generally just means a lot to me.). In the end I decided to put Monogatari on top because of the meaning it has to me but whenever I look at my list I still start having my doubts.

Have you ever experienced this and how did you tackle it?