Practice good daily backups via cron. I use Tarsnap and can bootstrap a new machine within 20min (dotfiles, scripts, etc).
If I leave the laptop on a bus or if it gets stolen, I just restore the tar.gz file onto another laptop, change the UUIDs in fstab and restore the home drives from backup.
PS: my paranoia level is quite low, I just don't want information about students available if I lose control of the device.
I'm pretty sure something like that is possible on Windows as well, altough you may need some kind of server to store the information so you can avoid receiving a mail or something with the information.
One thing you could to get your name and phone/email laser engraved on the bottom. This will fuck up the resale value and if it falls into the possession of someone honest they might return it. Or the thief might try to extort you and you can just show up with the cops.
Put sshd on port 443 on the VPS to maximize chances of a successful connection, and maybe put a bit of effort into hiding autossh on the laptop.
This way you have ssh to your laptop at all times. You will also know the IP it is on, for easy geoip lookups and tracerouting.
Whether such system exists, I don't know. Perhaps others can advise.