Don't know about Outlook 07 but to do it on Outlook 13, I use a program called Akruto. It syncs directly with Outlook via Wi Fi or internet. The same program offers built in an android and Apple method as well.
Don't know why MS has made it so difficult. I suspect it's has to do with MS wanting you to use the CLOUD. Outlook.com syncs directly with the phone but Office Outlook goes through some girations to do the job.
Hopefully someone else can offer more options.