I think using tails is the worst idea. If someone finds the usb drive, it is way more incriminating since it's the number 1 touted thing to use on the dark net. And packages of drugs + flash drive with tails on it is pretty incriminating. But if you have an encrtpyed VM that could be for anything (good or bad, it could be argued it's for work much more neatly than tails is). Provided you live in a country where you can't be forced into revealing your decryption passcode.
edit: So I would use EncFS to encrypt the guest OS volume. So basically
- Mount the encrpyed drive using encfs.
- Go in through virtualbox or whatever and select the guest OS from the mounted (decrpyed) drive made by encfs.
If someone got to my computer, they would only see gibberish files that encfs has, they wouldn't even know it is a VM volume in there. So don't have to worry about discarded the usb drive as there is none.
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