I assume you're using IMAP?

Has your situation ever worked properly, or is the problem recent?
How many email accounts are you working with? Please tell us the other ISPs, apart from Gmail.
How large are your accounts? Big accounts could take a long time to sync.
What's your internet up/down speed like? Maybe your bandwidth can't handle the syncing.

Without further info, I only have 2 suggestions:

1. Try making new account(s) in Outlook for each of your addresses. There may be some corruption in your current accounts.

2. Consider switching from IMAP to POP.