Bash on Windows is a fantastic tool. If you have not heard about it I suggest a bit of Googling but in short, it is a fully fledged (well almost) Ubuntu system running right on Windows. I don’t intend to repeat what is already out there so a couple of resources to get you started;
What I will say is that the single thing it has made so simple is moving files between Windows machines and a Pi. A simple rsync command and you can move as many files or directories as you need.
If you want a good guide on using rsync I found this does the trick; http://www.tecmint.com/rsync-local-remote-file-synchronization-commands/
One thing I did struggle to find, is where the Bash user’s home folder is under windows; for reference, it is found here:
C:\Users\[Windows User]\AppData\Local\lxss\home\[Bash User]
The lxss folder is a hidden one so you will need to change that in the Windows Explorer view settings.by