So if you are switching to primarily MS services as your source (WP8, W8, SKydrive, etc then you want the MS account to be your primary source for contacts, calendar, etc. It will also be your Windows (and WP) Store account as well. You need to migrate your contacts to your MS account (outlook.com) then whenever you add/change contacts and such on that account they will auto sync across all devices that are using that account. I assume you are adding contacts on the Android device to a gmail account which is aggregated to the Surface because you have both accounts in there, but when you add new contacts on the Surface it is to the MS account which isn't setup on your Android device so you don't see the cross platform sync. You want them all on one account so they will manage easier across devices. Hope that makes sense.