The support community had this bulletin. Started at 1:52 and ended at 4:07pm. Might be related. Might want to leave a message on their support forum. »answers.microsoft.com/en ··· l?auth=1
Thanks for the post, although that doesn't seem to be directly related as my problem still exists. I did a chat with MS before and after he tried redoing my whole Outlook profile, he concluded that it's probably a server problem and is reporting it. I find it odd that I haven't seen many other people mention having a problem on various sites, but my account isn't loading on a second computer when I set it up. Hopefully it'll be fixed tomorrow.
Outlook ended up syncing all of a sudden in the afternoon of the next day. Apparently it was just a server side issue. I probably should have waited a day or two before wasting hours trying to fix it.