[Speaking as Debian co-maintainer, Ubuntu is of course absolutely free
to change the packages as they see fit.]

> Configure Wine
> Uninstall Wine Software
> Browse C: Drive

... for these I personally see no need, and when I asked in the past
nobody was interested in sending these Ubuntu specific files to
upstream.  OTOH I'm also not aware of any risks or problems with those.

> "Open with Wine Windows Program Loader" link

First off, I absolutely get your point how this is unfriendly for users, 
especially inexperienced ones, in the first place.  But this is only useful for 
applications which work flawlessly without the need for any workaround 
(applications which are rated platinum on appdb.winehq.org).  Unfortunately 
these apps are only a very small part of all Windows applications.
So instead of giving users a very easy start in using Wine, followed by a big 
disappointment if the installation fails silently or some later issues exist 
... instead of that I think it's better to look up the Wine instructions for 
any Windows application on appdb.winehq.org first. Getting users to be aware of 
this ressource imho is much more needed and helpful.

Now, back to the topic and the main reason why this doesn't work:  "Open
with Wine Windows Program Loader" is done by the wine.desktop file.
That is already part of the wine-stable package, but not activated for
security reasons. Quoting /usr/share/doc/wine/README.Debian.gz:

System and desktop integration
You can configure your system to automatically launch Windows executables.  But
this increases the risk of inadvertently launching Windows malware, so please
make sure that you understand the security risks before blindly setting this
You can also make Wine known to your desktop environment.  Then you may for
example in a filebrowser double-click on Windows executables to start them, or
right-click on them to "Open With Wine Windows Programs Loader".

To enable system-wide support for .exe files execute the following command
(replace /usr/share/doc/wine with /usr/share/doc/wine-development if you use
$ sudo cp /usr/share/doc/wine/examples/wine.desktop /usr/share/applications/

To support this only for your current user execute:
$ cp /usr/share/doc/wine/examples/wine.desktop ~/.local/share/applications/

NOTE: I just realized that this documentation should refer to 
/usr/share/doc/wine-stable ("-stable" is missing.  Only Ubuntu 16.10 to 18.04 
are affected, later versions will have a regular "wine" package again.)

Suggestions how to improve the overall situation are very welcome,
including places where things should be documented (I guess not many
Ubuntu users are aware of /usr/share/doc/...).

This topic should be marked "Won't fix" from my perspective. Sorry.

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  wine-stable is missing the standard Wine menu entries / .desktop files

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