I need an Outlook specialist

several problems with multiple files in outlook - if I click "To" in an email, it doesn't bring up the proper contact file, nor does it offer the option of the correct file (I can only get my contacts by clicking the contact icon. Also, similar problem with calendar. Need help understanding the heirarchy of my overburdened files and folders. I'd like someone who can connect to my computer and talk with me by phone stat if possible