Have a look at Linux Mint. It's based on Ubuntu, so you get full compatibility (which is good, since Ubuntu is targeted by many developers) and solutions to any issues can quite reliably be found by doing a quick "Ubuntu problem xyz" search. It comes well configured with everything you need to get started out of the box, it's stable (based on Ubuntu's long term support version) and has its own very helpful community. Definitely a good place to get started.

Mint's default desktop environment "cinnamon" will also feel a lot more familiar (and functional) than Ubuntu in its default setup. With cinnamon, you get a taskbar, a start menu, a system tray with a clock next to it and so on. Unity (Ubuntu's default environment) imho feels more like some kind of desktop/tablet hybrid UI. It is disliked by many. Other decent choices include KDE (my current choice, needs customization to really shine but is extremely feature-rich), XFCE (a simple environment that gets the job done, is pretty light on resources and can look good with a bit of tinkering) or LXDE (really fast and light on resources, but visually it'd be Windows98 all over again).

Erm, sorry if this was a bit too much of an answer to a question you didn't ask. Basically what I'm trying to say is that Ubuntu or (especially) Mint will be fine, but don't get scared off by Ubuntu's Unity. In any case, Oracle's Virtual Box can be downloaded from the comfort of your software center and running Windows in it should be trivial.