Are you sure Outlook does not support batch imports of .vcf files? In the version I have installed, I was able to drop multiple files onto the contacts view, and it imported all of them correctly. There may be extenuating issues with various versions, but try more than one way to import before doing a lot of work.
(Hmph. I could have sworn that I replied to this a couple of hours ago.)
Well, in the version of Outlook that I was using, it did not allow me to drag a cluster of vcf files to the Contacts pane, and the open dialog didn't support multiple choices.
I take it from your comment that you used the drag-and-drop method?