For me, I think it's because I can't do anything at night - pay bills, run errands, normal life stuff. I mean, I can pay bills online, but that's beside the point. I don't HAVE to do anything at 2:30am so I can just BE. At least, that's my theory.
Well, we went to the medicare site, used their 'find me a plan' function, and signed him up because he's been going all these years without any prescription coverage. I don't know how his case manager got rid of the late enrollment penalty, though, but apparently she did.