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Why do Tor experts discourage using Tor and a VPN at the same time? Is it because of the network fingerprint, latency, or that there is no point to it?

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Well, it's totally not a problem - using Tor with VPN, but:

  • Use direct connection with static IP address and ORPort opened, it will help. Also keep your node running 24/7
  • If you can not connect to directories(banned by IP addresses and/or protocol DPI filter) - use OBFSv4 bridges or set your router box up with VPN the way that directories will be reached via VPN but other addresses are not
  • Run DirPort directory mirror, so it will help the consensus

That's actually when and how you can have a benefit using VPN with Tor. Other scenarios will not break things up, but will not make any profit too. A quick note - about the non-reachable ORport through VPN: quite a lot of nodes do not have ORPort reachable, like ones behind the NAT, so it does not make a sensible difference.

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