I don't know how to do this from Windows, but you can do most of what you described with a GUI in Ubuntu.
This is how you can avoid having restart Windows Always Boot to Ubuntu
Perform the steps below. After those steps restarting windows will always boot to windows automatically. Restarting Ubuntu will always reboot to ubuntu automatically. You won't have to edit every time. Just configure Grub to remember the last choice. The last choice will always be the automatic default with not further manual changes each time.
Install the GUI Grub Customizer.
$ sudo add-apt-repository ppa:danielrichter2007/grub-customizer
$ sudo apt-get update
$ sudo apt-get install grub-customizer
From the GUI you can choose which Boot will be on top by selecting it then click on the Up/Down arrows to position how it's listed.
Under the general tab you can further customize Grub's behavior. You can also click on
Advance to change enable, disable, add, remove, or change the lines of the grub file.
The temporary booting to Windows part can be achieved by:
1) Select the GRUB_DEFAULT entry -> Click the Value Column. Replace the "0"
2) Add an entry named "GRUB_SAVEDDEFAULT" -> Set the value to "true"
3) Now click Close -> Save (When you click save Grub will be updated to your new
Now after Windows is rebooted it will not go back to Ubuntu
Now when you are performing Windows Updates and other Maintenance the system will always boot to Windows (once you have booted Windows) until you Choose Ubuntu to go back into.