It can be done using a host and a VM where the VM connects thru the host. Both the host and the VM will need a VPN. Latency is an issue. If a VPN drops your connection you real IP number can be exposed, however that can be controlled with a properly configured firewall. Pay for those VPN's with washed Bitcoins or Liberty Reserve, some accept cash in an envelope (Mulvad).
Being anonymous is not as simple as installing a VPN. Check for DNS leaks »www.dnsleaktest.com/
Long Thread at Wilders relating to anonymity: »www.wilderssecurity.com/showthre···t=285780
Have a look at Dropbox: »www.dropbox.com/