How is contact syncing work between Outlook Desktop and WP (MS Account) meant to work?

I’m considering a jump from an iPhone4 to WP, but first I want to be sure that my large contact list (with extensive notes) in Outlook 2013 will sync properly.

I’m disappointed to see that there is no direct sync between Outlook and WP (which is perplexing given that the iPhone will sync with Outlook) so I’ve tried copying my Outlook 2013 contacts to my MS Account as described here.

So, I now have two identical contact lists (except notes formatting which does not appear to be supported in MS Account contacts), one in Outlook 2013 and one in my MS Account. Am I supposed to now delete the Outlook 2013 contacts? I believe not as I noticed that some of the contacts were somehow related (note, not linked that appears to be something different) so that if I changed a contact in one list, it would automatically update in the other but there seem to be many issues:

  1. Not all contacts update their counterpart in the other contact list and I can see no logic as to which contacts update and which will not.
  2. The updating only seems to work one way – if you update the MS Account contact then the Outlook 2013 contact gets updated, but not the other way round.
  3. Updating only seems to work properly if the contact is opened via the People view – if it is opened via the list view (which has more options/fields) and edited, you then have to resolve the differences the next time you open the contact from the People view (for changes to Notes at least).
  4. If you open your MS Account on the web and go to People there is an option to clean up your contact list which pulls in information/photos for your contacts from other services such as Linked In and Facebook. Very neat but the information/photos don't seem to be reflected in your MS Account contact list in Outlook 2013.
  5. There is nothing to indicate how or when contacts sync between the MS Account contact list in Outlook 2013 and People on the web (does this happen when send/receive is pressed?). I experimented with deleting a contact in MS Account contact list in Outlook 2013 and it did eventually disappear from People on the web, but changes made in People on the web have not propagated back to the MS Account contact list within Outlook 2013 despite hitting Send & Receive multiple times and waiting more than an hour.

So I now appear to have 3 separate lists to try to manage – Outlook contacts, MS Account contacts in Outlook and MS Account contacts in People on the web (I’m guessing this is pretty much equivalent to the contact list in WP).

Am I missing something fundamental/obvious here? How do other people who use Outlook and WP manage their contacts? So far the whole thing appears to be a mess and may well stop me from moving to WP despite how much I like other aspects of the OS and hardware. I just want to be able to share contacts between Outlook 2013 and my phone and have changes made on either one sync back to the other...