I use Outlook (desktop) at work, where I have setup both my work email and Hotmail email accounts.  I have separate calendars for each, and I also access other users' work calendars through the Outlook desktop software.  (I have 5 calendars showing.)  However, when I enter calendar events on the calendar associated with my Hotmail account, the events do not sync with the web Outlook.  That is, the events do not show up on the calendar available at outlook.com.

Additionally, the events on my Hotmail calendar on the desktop don't sync with my iPhone, regardless of whether the phone is connected to my desktop via USB or not connected.  I don't know if this problem is related to the above, but I suspect it is. 

I've tried to enter a test event on the web calendar, but it tells me to "wait until calendars have loaded before saving an event."  I don't know what this means, but the calendars never seem to load...  I've created a 'test' event on my desktop personal calendar, and it does NOT appear on the web or on my phone, and I've put a test event on my phone, and it does NOT appear on my desktop or web calendars.

In case it matters, I am using Outlook 2010, Mozilla Firefox for web access, and iOS 7.0.2.  I hope this is user error and that you all can guide me to syncing the three calendars.  Thanks in advance!
- Brian