Let me be among the first to chime in... Their spam filter sucks big time.
For the past 6-8 months (or more), I've been getting spam for all sorts of services that originate from the same sender. They use the SAME template! It's just a series of images, with THE ONLY TEXT being "Can't see Images? Click here". I marked such sh!t as Junk countless times, only to come back the next day to seeing some of the same ones in my Junk filter, some in my Inbox.
It doesn't matter that the subject line is the same - advertising for Match.com or some other crap, even though I mark it as Junk, apparently Hotmail does not even pretend to do anything about it. Same subject line, same template with images only.
THIS IS BASIC SPAM FILTER 101, if there is no address, or Unsubscribe in the newsletter, or a poor text to image ratio, IT IS SPAM! What the hell is their spam team researching?
And it has the most worthless spam configuration settings: all off, the useless "ON" setting, or the idiotic "exclusive" from your contacts only.