Outlook Calendar sync is intermittent

Windows 8 pc w/ Office 2010 with icloud syncing my calendar and contacts, but in Outlook - quite randomly and intermittently - the icloud calendar comes up blank (showing no appointments). This randomly goes away, sometimes after a few random clicks, sometimes not though after much hoopla (close/open outlook, wait an hour, etc.). It does always eventually come back, but it is a time waste trying to use my desktop to set an appointment that will sync, as it leaves me having to come back later to enter it (or check it/input it on my phone).

Been an issue for a year, and I've done all the good local detective work on looking for behavior commonalities/reasons why. Any help?