Calendar syncing with Outlook is possible, though somewhat kluge to set up. Once set up though it will automatically sync. Here is how I did it on my Android devices.
Set up a Google Calendar via the internet. (You can do this via your PC.)
Install and set up Google Calendar Sync on your PC. (This allows Outlook on your PC to sync with your Google Calendar.)
Install an app like CalenGoo on the Kindle Fire and set it up to sync with your Google Calendar. (The calendar app you install must be able to sync with Google Calendars.)
Basically you are syncing your Outlook calendar to your Google Calendar then syncing your Google Calendar to CalenGoo on the Fire. As i said it is kluge but it works automatically after you get it all set up.
For Windows 7
Try this: In Windows 7 - Search your computer for the word "contacts" and a folder should show up with all your mail contacts in it. It is NOT the same as the contacts folder within the mail application itself, the folder where those contacts are kept on your computer. Open the folder, and along the top bar of the window there should be either an import or export link. If it's an import link, it will have a little arrow down and export will be another option. Click export, and export your contacts as vCard. Follow prompts. I had it export them to a desktop folder. Once contacts are a vCard file, you can use a usb cable to move drag the file (s) to the download folder on your Kindle. You cannot mail vCards to the Kindle.
Disconnect your Kindle (safely) and go to Kindle Contacts app. Open it and from the bottom menu select Import/Export, then Import from Internal Storage. It should go find your vcard files and import them into your contacts. The mail app will also have these contacts in it when you open it.
2. Another easier way is to try and import them into a gmail account. Then you link that gmail account to the Fire.