Have you ever checked click-once? A superior windows like installer for .net.
It completely eliminates 1).
It completely eliminates 1).
Msix is better, but still not well supported - you can deploy a service for example, but not on a windows server.
We deployed click-once in an Enterprise env for internal apps though. Didn't had much issues with what you mentioned.
To debug/install windows services, we combine them with TopShelf - http://topshelf-project.com/
( Ah, perhaps 'windows like installer' could be misleading. I meant windows only, but like a 'installer' mechanism'. Since it installs, updates, ... Out of the box. Didn't exactly knew how to write it as short as possible)
(Then you could get the same critiques as java web start.)
It's a great experience in Windows though. We have multiple internal applications running on it.
Although it's not a one size fits all solution. But internal apps that can leverage windows are extremely quick to setup with the winforms/click-once combo.
Shared network drive and everyone has an installation + auto update mechanism.
( But i guess that combo isn't popular here )