Dark web…

There is no one or specific Dark Web - sure you can hop on TOR and find a bunch of stuff you won't find on Google but that is just window shopping really compared to what is out there.
 
Make a tails/whonix VM or USB.
He didn't say he was committing cyber crime now did he?

The idea of using Tails in a VM haunts me. Buy a $5 laptop from Facebook marketplace, remove the CMOS battery and hard drive (curse you NVRAM). Move far away from entry and exit points, preferably also have an alarm system for intruders/glowies, but also have an exit in mind. Make sure you have a microwave close by too. Boot from USB.
 
The 'dark web' is a nonsensical term given to sites served outside of the traditional web. There's nothing inherently bad about it, and in fact it (Tor) is used every day by security services, law enforcement, journalists, whistleblowers and all kinds of regular people. As above, BBC have a Tor website, so do most search engines, and so do many online services. It's a decentralised, censorship resistant and democratic system with cryptographically signed endpoints, making it very useful for privacy and anonymity.

I run several Tor exit routers, guard/middle relays and bridges/proxies, and have done for some time. All you need to do is download the Tor bundle and away you go. You'll find it harder to navigate compared to the 'regular' web, but there are directory services out there. Brave Browser bundles Tor abilities, and can be set to automatically open any Tor-accessible websites (DuckDuckGo, BBC, whatever) in a Tor session when they present themselves. Be aware that Brave is not Tor, and doesn't have the same privacy or security assurances. It's fine for casual browsing but don't trust it (Brave) for anything serious where your anonymity or privacy are essential.

Edit: BTW, @red eye you don't need a VPN for Tor. Using Tor is its own thing, you don't need to further tunnel a VPN over it, or it over a VPN. Be aware, however, that only the Tor browser is protected when running Tor, it's not system-wide like a VPN.
 
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