Hello,
I don't think there is a way to have VisualCron automatically start a service when the server reboots. There is a way you can get around this though. You could create a program that automatically starts with Windows and opens a simple flat file, modifies it, then saves it to the disk (for example: C:\StartService.txt). In VisualCron you can create a file trigger that watches the file for changes. Once the program saves the file the job will start and from there you can have it start the service. One suggestion I would have for your program is have it wait, say, 30 seconds before it modifies your file. That should give Windows enough time to start the VisualCron service. There is a little work involved however someone else may have other ideas.
The second part of your problem is easier. You can create a trigger that watches the status of the service. When the status is "stopped" VisualCron can restart the service.