Hello Ross, thanks for this guide on how to achieve caller-ID, iMessage, etc. while having a working two-way sync of contact details. But how about password changes, does the user needs to change the password in Outlook and in the native app / profile? Also why can´t there be some kind of solution on Apple´s end, to get caller-ID working with third party apps like Outlook? Our enterprise strictly separates company data and private data on iOS and Android devices (far better on Android because of work profiles), thus syncing to the native app also enables other un-managed apps to access company data like phone numbers (e.g. WhatsApp, WeChat, you name it). It´s kind of a struggle to handle company contacts, either you are following GDPR (we have several branches in Europe) and have it separated or you have the comfort of having caller-ID
I hope there will be a real solution and Apple gets something like Android Work Profiles 
Mike