Although its not exactly what you asked for, I think I have an alternate solution for you.
VirusTotal is a subsidiary of Google and has an app that integrates into the Windows Explorer context menu. This will send a file (up to 5 at once) to be scanned by 54 different virus scanners and give you the results.
I find this program to be extremely useful when downloading a new application installer from an unknown source.
It is probable you can create a single context menu entry to combine multiple context menu actions. The problem lies with how each application handles the context menu action. You could figure out how each one works and then create a custom context menu entry.
However, I think I have a better solution. You can use AutoHotKey to execute multiple context menu actions in a script. I do not think it would be to difficult to create a script that opens the context menu and then triggers multiple context menu actions, or even use the arrow keys to cycle through the menu to execute context menu actions.