One very important thing not mentioned is that the tor exit node could be capturing your traffic or do a MITM attack. Its a great idea for testing but only after you have encryption working, and of course pay special attention to your ssh fingerprints.
If the endpoint is in your control and you'd like to experiment with Tor, you can configure your server as an Onion Service, so you are protected by Tor's own end-to-end encryption (whose traffic cannot be captured by MITM since the hostnames themselves are the public keys). For non-anonymous uses, you should active the "Single Service Onion" mode, so the 6-hop (extra 3-hop for server anonymity) is skipped, allowing standard 3-hop latency and performance. It also saves bandwidth for exit nodes - all non-exit relays can forward Onion traffic.
Hidden services are not accessed through exit nodes. Relay nodes cannot capture your traffic or perform MITM attacks.
Cloudflare is mitm, btw.
So is your network firewall, what's your point?
Cloudflare can see decrypted content when HTTPS is used.