To install Messenger on Linux or pre-Catalina macOS with Wine, start by installing the following dependencies through winetricks:

• corefonts
  
• gdiplus
  
• msls31
  
• riched20
  
• riched30
  
• tahoma
  

These dependencies will install the necessary text and graphical components needed for MSN Messenger to operate properly (i.e., UI font, email/password boxes, message pane in conversation windows).

There are also msxml3 and Flash winetricks, the first one also required to run MSN Messenger and the latter being optional. But those presently have issues, Messenger-specific or otherwise:

• The msxml3 winetrick as of writing this fails to download as it's retrieved from an inaccessible FTP server. Just download from NINA storage and run the file through "wine msiexec" to install.
  
• The Flash winetrick will not work anymore as the download server the Flash Player installers were downloaded from are no longer accessible. I wrote a guide on handling the installation of this on this guide. Just apply Wine concepts while performing the instructions since I wrote it under the assumption that the user reading is using native Windows.
  

'Messenger/msmsgs.exe'
'MSN Messenger/msnmsgr.exe'
'Windows Live/Messenger/msnmsgr.exe'

With the newly added Messenger setting selected, change the Windows version to at least Vista or higher and apply changes. This will allow MSN 7.5 and above to run without crashing.

When you're all set, run Messenger if it isn't open already. By now you should be able to log in and use the service almost normally. Most features that aren't already broken as a result of Escargot's implementation of services should work, like adding contacts, receiving status updates from contacts, messaging, display pictures, background (and possibly file) transfers, and tabs. Only things confirmed to not work so far are handwriting and games, but those in the long run are very ancillary features and fixes for these issues aren't a top priority of anyone else on the Escargot team.

Any feedback regarding this guide is welcome in the replies, and I hope this helps people who pretty much don't have native Windows as an option.