In all the years I have had smart phones worth insuring, perhaps about 3 years, I have never filed a claim. I am likely never going to file a claim and depending on the phone of choice I like working with and if that phone is still available third party for a good price, I sometimes cancel the insurance if I think I can go a while before getting the next phone. I don't necessarily upgrade every 2 years, but will if there is a compelling device better than what I have. (With the GN2, the bar is raised this time for sure.)
So for me, understanding the differences between Asurion and Best Buy, for me Best Buy was by far the best choice. Its less expensive per month and a replacement, in the very unlikely event I need to, is free. Also, after I understand more about my options and I see root alternatives that I want to use, I will be rooting the phone. If I mess up a phone because of a failed root, Best Buy will take it back, I don't know what Sprint/Asurion will.
This is the first one I have insured through Best Buy, so it remains to be seen if I will actually like it, if the insurance is necessary, but I am definitely happy with the choice I made thus far.