Organizing and accessing contact information in Outlook.com
I'm surprised to see this re-emergence of the "disappearing groups" problem. After my outlook.com account was migrated to the new version mid 2016, things have been very stable. I will say that I am using Microsoft Office 2016 Outlook to actually manage the groups, rather than the web application, and this also gives me the safety net of saving a backup. If I was using my outlook.com for business or more critical applications, I'd certainly go that way, or one step further into the professional version of Office 365.
However, my biggest distro group of about 120 addresses has behaved well. There are a couple of anomalies which relate to some of the recent posts... If someone has a change of email address, and I change it in Office Outlook, that change is mirrored to outlook.com BUT I need to remove that contact from the group, and re-insert it with the new address. I noted also that when updating a contact's email (again in Office Outlook), it pays to click on the dropdown on the email line to see whether the contact has more than one email address. On at least one occasion, this explained the old address "persisting" when it should have disappeared.
Not sure, InkmastersCairns, what you mean by not being able to send to multiple addresses. You can do this by your groups/lists, and by simply adding more addresses in the To: line in the web client. The cursor goes to the right of any previous address you inserted, and usually typing the first couple of letters of the name will do the trick. Alternatively (again in web Outlook), in the People page, you can check the boxes that appear left of the person's name when you hover mouse over it, and when you have checked all the ones you want, you'll see that an icon has appeared on the right pane, with a "Send email" option to the selected addresses.
I do think, though, that for people who only use the web based outlook.com client, there should be a better and more obvious way to export/save/backup your groups/lists. Come on, MS! Fix this!