Issues with accessing SharePoint Files though Web Dev

We've found the webDav option (explorer view) to be extremely buggy and getting worse.  For our users that need to interact with files in Windows Explorer, we tell them to use the OneDrive desktop app (aka sync client).

I referred to this support article a lot because most of our issues were simply opening it (https://support.microsoft.com/en-us/help/2629108/how-to-use-the-open-with-explorer-command-to-troubleshoot-issues-in-sh).  One thing that we would see that might be related to what you have is that logins would time out and create issues with opening / saving documents eventually.