Organizing and accessing contact information in Outlook.com
I share your pain and see no fix in the short term. I too will clean out all contacts on my Mac Outlook 2016, on my Outlook 2013 and on Outlook.com. I purge everything from the "Deleted Files held for 30 days bin". I import fresh and verified contacts csv file with 241 contacts. All fine and I check everywhere and it is 241 with complete contacts info including categories. Wait a day plus and I now have 5275 contacts. I think I need to call Mulder and Scully for this problem because anything they come up with is going to be better and more entertaining than what we have already.
I migrated to my GMAIL account and have my outlook mail forwarded there. I have also made the outlook.com mail address as default in GMAIL so my responses will have the Outlook.com address despite coming from GMAIL. This is a compromise I will need to live with as at least I don't have this weird contacts problem with GMAIL.
The other thing that Outlook.com drove me batty was that despite the nice style and appearance, the display would always shake or tremble, not all the time, but enough to make it uncomfortable. It is not the laptops as it does it on my MacBook, Windows laptops, and Outlook for iOS. Almost as it was suffering from too much coffee! Also, my folders would disappear and reappear after a refresh.
Again none of the problems mentioned above happen with my GMAIL account (I use the web access via Chrome). So I guess this is the way it will be for the time being.
By the way, I don't think I had this problem prior to the migration to the new Outlook.com setup. I think the old style and even when in Preview mode, I was spared the joys of these issues.
FCG