> First, I am not sure if I need to create a home widget (?) that will first check the network connectivity and start the VPN if required and THEN start my app (DS Photo for example) once the VPN connection has successfully been established..? Or should I just have tasker monitor when I launch the following 5 apps and apply those rules?
>
Depends on what you want. If you want to make sure you are connected 'Before' the app starts then you would want to use a 'Task short cut' from your home screen to test connection and then start app. If it does not matter if the connection is made after the app starts then monitoring for those specific apps would be better.
Use a task short cut if you just need to start a task from home screen. you would use a widget if you want to interact with the icon on the home page (IE change the icon when app is running)
To Kill A app you will need root. I am not sure How clean it is. You can background the app by using the action / app / go home.