Question about Outlook Express

I have an iPhone, and it syncs with Address Book, and I have sync services turned on, but I can't seem to find a good way to sync Outlook on laptop and iMac, and Address Book.   I continue to get data moving around to different fields, missing data, no data, duplication, etc.

I also learned that if you manually enter contact info in Outlook, it won't get pushed back out.  This is a problem in the sense that I have Outlook on my laptop and my 27" iMac at work, and this results in an inaccurate address book.

I don't understand why Microsoft and Apple can't come together to have a better way to sync address book data.  Everyone I encounter seems to have an issue with this.  

And speaking of Outlook, why is it that Microsoft had to try to reinvent the wheel in the layout / design of meeting notices?  what's wrong with how Outlook 2010, or 2007 for that matter, work?    I hate the fact that if I want to add people from my address book i can't simply select TO or CC or BCC and my email addresses come up like they do for the Windows version.  Instead, we have to move to the far right hand side, select the image of an address book which then takes you to Contacts Search, and then you have to choose the correct drop down, etc.  Who would design such an inefficient solution, particularly when 2010 was already out, and it works fine?  Why take a completely different approach?

Most people using Office on a Mac do so because they have used or are using the Office on a Windows machine.  Therefore, that's what they are used to.  

Outlook 2011, for me, continues to be the single most frustrating, crappy Office product of all of them.  And I'm not in the Apple vs Microsoft camp - I just want what works best.  I use Office365, and all of the tools there too (SharePoint, Lync, etc.).  And I'm happy with them, for the most part.   

BTW  - I have tools like Contacts Cleaner, etc.  But I'd rather get a fix for the problem to begin with, rather than a bandaid.