[qx24b]

As long as you don't really need to interact with windows more than a shared folder I'd go with virtualbox headless.

Since it is a laptop you can set it up to have one network card be NAT for the internet and the second be host only so you have a dedicated local ip to hack on no matter what network you are on.

I believe my setup when I did this was the first card was NAT with dhcp and the second card was a static ip and I believe all you needed in debian was to specify the address for card 2.

vmware has the option to start on boot though and it might work better for headless servers, I haven't used that in a long time though.