Outlook.live.com is not an email client, it's a proprietary webmail interface. It has literally nothing to do with the Outlook desktop program. It's not a replacement for it.
If you are just managing email, I highly recommend using a "real" mail client like something Thunderbird based (I use the MailNews fork of Interlink Mail and News). Setting is up is a real pain compared to Thunderbird but the UI is so much better. Mozilla, Microsoft, Google - all their products have pretty much turned into garbage in the past few years+.
The only reason Outlook is needed is for Exchange, particularly calendaring, contacts, etc. which are all the Microsoft Exchange protocol, so you need *a* version of Outlook. Any version, if you have on-premises Exchange, but you're stuck with 2013 or newer for the Microsoft account (free) email services.
Google seems to have done something similar, by the way, where they are blocking less secure access, although they have delayed it for organizations. There seems to be a concerted effort amongst Big Tech companies to move away from long established "standards" like POP and IMAP and force people towards proprietary software or interfaces that will guarantee vendor lock-in or recurring revenue. There's seriously been no good software released in the past five to ten years, by any company, so this is yet another way of convincing people to buy something they don't need or want.