I found a good fix/work around for this issue: don't manually change the settings of a custom view. For example, when a Custom View is applied, do not re-sort by Date or From, and do not enable or disable the conversations view manually.
Here are the steps to fix:
- Open any mail folder.
- Choose the default view (Compact on my computer).
- Manually change the view like you want, e.g. set the sort order, enable or disable the conversation view.
- Click on View / Change View / Save Current View As a New View.
- Name the view.
- Choose "All Mail and Post folders" (or another option if you prefer).
- Press OK.
- Go back to step 1 and create a another view, do this for all of your commonly used views.
Now when you want to switch between views just switch to one of your newly created custom views. Be careful not to manually change anything while your custom view is enabled, if you do it will change the custom view's settings. If you want to change some view settings without changing your custom view's settings then switch back to the default view (Compact for me) and make the changes there.
Note that to make this more efficient I added the Change View button to the Quick Access Toolbar in the top left corner of the Outlook title bar. Now I'm only 2 clicks away from my most commonly accessed views.