Joe recently bought an iPhone and iPad, but there are programs at work that Apple doesn't support. So he's using his old HP laptop for those. Now he's having issues syncing calendars and contacts, and Apple hasn't been much help because they don't support Microsoft.
Leo says the good news is that Microsoft just updated Outlook for Mac and he can use that. Sync is hard and often it'll only work once or twice before failing. The problem with his iPad and laptop is that they act as two masters, and Outlook just saves them both. That's why Leo likes to keep everything in Google. It just works.
Leo recommends using GSyncIt for the HP. He should have the Mac sync to Google Calendar. Then make Google the master and sync everything to that.