I understand that there are many pros and cons to pursuing a masters at the same school you took your undergraduate degree at. In my particular situation, I am a Canadian fourth-year undergraduate student in Philosophy, and I've recently been approached by two professors who personally asked me to enroll in the Masters program at my current school - and one of which has offered to work with me and supervise my thesis if I do choose to study there. This professor is someone I've worked well with in the past, and whose particular area of interest intersects with mine. Given the strength of their recommendations, I'm sure their references will be very beneficial, and it would be exciting to work with a professor whom I already have a well-established relationship with on a project that interests me.
At the same time, I am aware that going to another school offers the benefit of a whole new roster of professors, classes, and research which I could be exposed to. While I am sure I could find professors with whom I will get along with at other schools, many of my friends who have gone to different places for their Master's degree did not have such luck (or did not find the professors at other, more prestigious schools to be any more outstanding than the ones at their own).
Although this question may beg the answer, "It's entirely up to you", I'm still wondering if anyone has insight into how important it is in this field (i.e. for someone who wishes to pursue a PhD/eventual professorship in Philosophy) to go to a different school for their Masters?