Something come up to my mind... Vulnerabilitys could be,
- the user forgets to start the VPN, or
- the VPN connection breaks down for some reason (Windows bug or crash), 
traffic continues without Tor

I like the basic idea of JanusVM. I can say nothing about the concept of the 
deployed virtual machine but those vulnerabilitys I posted here could be fixed 
using a software firewall in whitelisting mode. Everything incoming and 
outgoing blocked expect the VPN connection.

Furthermore the VPN connection and the firewall should be forced enabled by an 
administrator and all applications should run as user. Not sure if that's best 
possible. Probable the Tor transparent proxy approach [1] is even better.

What I liked about JanusVM is that it's very easy to install and use.

[1] https://trac.torproject.org/projects/tor/wiki/doc/TransparentProxy
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