For calendar, use Google Calendar Sync (which now supports Outlook 2010) to sync your calendar to your google calendar, then it is automatically synced from google to your phone. You can then add events anywhere and your calendar will sync across your Evo, Google, and Outlook.
For contacts, i don't know of a simple easy solution to automatically sync. I have just imported my contacts into gmail and they sync between my phone and gmail. Eventually it would be nice to have them sync to Outlook, but I haven't found a solution.
If you wanted to manually sync, you could just import your contacts into gmail from outlook and export from gmail and import into outlook. This is only a one way sync though.