MS Outlook by default keeps all your mails, calendars, task, etc. in one big file. Normally it's called Outlook.pst. So the first idea one might have is to copy this file over to the respective other pc. And yes, this would work. But it's a bit difficult to find the pst file. Here's how to:Double-click Outlook > Open the tree with your folders > Right-click the root item > Click on "Properties" > Click on the button "Advanced"

Here one can find the full path of your pst-file. You can simply copy it to the other pc. If you want to automate the transfer of the file, you can use Easy2Sync for Files (Freeware Edition). Note that you can only copy / replace this file while MS Outlook is closed.

However, one can only copy the file while MS Outlook is closed. And whenever you replace the Outlook.pst file, you should know that you're replacing the entire contents. This can be a threat if you made changes on both computers since the last copying.

So you require something different. Copying the file isn't enough. You need to synch the file's contents. Bad news is: You can't do this by copying files. You need a special tool to to the job. But the good news is: There's a fantastic tool out there that does the work for you. It's called Easy2Sync for Outlook. The tool is specialised on Outlook sync tasks and does all the work of watching where things have changed and copying the changes. So you don't need to copy files any longer, you only need to run the sync. And you don't need to remember which pc owns the most recent version as the sync tool will automatically handle this for you.

But that's just one of the advantages. This sync tool also allows you to exclude a part of your contacts from the sync, since you're not copying the complete file any more. You can for example exclude Outlook folders that you don't need, or limit the sync to your tasks. Or you can sync only the private tasks and so on.

So, a good sync tool like Easy2Sync can save you lots of time. Manually copying PST files can be an easy beginning for trying things out, but to work every day you need a real sync tool.