If you do it with Vagrant it's not painful at all because you can then make easy directory maps to access the files. I've done this for years.

Windows 10's WSL (Windows Subsystem for Linux) is pretty amazing though. If you're only doing command line stuff, you might be able to get almost everything you want done with that instead. I managed to configure mine to run my tmux and vim configurations, get Ruby running, and install the Ubuntu version of Vagrant to provision some DigitalOcean machines. It all worked relatively easy.

The only stumbling block I ran into is that the Bash shortcut doesn't drop you to a login shell, so my .profile wasn't executing. From Powershell, start bash with --login or append --login to the Bash shortcut, and everything works pretty darn well.

But if you're gonna go the VM route still, just make sure you have tons of RAM. My 4gb Surface doesn't do a horrible job, but after the summer Windows update, I feel the pinch more than I used to.

Hope that helps!