I don't understand what you want to do, but here is good OPSEC:
VPN > VM > TOR > PROXY
VPN: Your ISP won't see you are using TOR, so you will never become suspicious. This should be set on your host machine.
VM: I recommend Whonix Workstation, a VM that is designed for privacy and security. With this you can isolate your work into a VM. You can even store the VM on a PenDrive
TOR: To connect to the web thru TOR, use the Whonix Gateway (all info on whonix website). The TOR will make your internet traffic encrypted and impossible to follow
PROXY: Some sites will act weird, since you are using TOR. (Google will constantly ask for captcha). To prevent this, use socks (maybe vip72.org). Use it from the VM. The sites won't see that you are using TOR.