Software Deployment

You need a Key Path for each component.

The way that the repair works is that it checks for each key path in each component. If you havent set one then there is nothing to check, the MSI wont know its missing, hence not being repaired.

One thing I have always wondered. Why make a REG dummy keypath for CurrentUser stuff when you can make a file the key path?
-saw someone else ask this, but there was no reply. Ive always used a dummy REG as I was advised it was best practice.

*Half correct in the repair feature statement, it dosent repair but checks the whole feature if there is a bung component.

Self healing from advertised shortcuts only checks the key file/path for components in the same feature (and any nested below) as the exe component that is being launched.  As a matter of fact, repair does the same thing, this is an important concept to understand when dealing with MSI packaging.  The difference between self-healing and repair is what is checked (the key file/path checking process is the same).  Repair checks all features and components installed originally.  Self-healing checks only the feature (and nested features) of the component which kicked off the self-heal (usually advertised shortcut exe but could be mime type etc).

The key above is the key file/path, if you have 100 files/reg entries in a single component it is all or nothing during a self-heal.  If the key file/path exists, the msi will skip the whole component, re-installing none of the 100 files/reg entries.  IF the key file/path is missing it will install all of them based on the additional rules in the file table.

Thus if you want to make sure every file is checked for, you will have to create separate components for each file, making them your key file(s) for each component.  So when the advertised shortcut is launched they are each checked (remember the components should be in the same feature as the exe/advertised shortcut component).

I have seen key files not work in advertised shortcuts, I usually use a HKCU reg entry.  Not saying files don't work, just HKCU entries seem to be more reliable.  For your case I would certainly test using the key files since that is what you will need.