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 Why not have both parties connect using TOR? 
 Sure you can do that. But the more hoops you need to jump through in order to get privacy, the more points of failure you have and the more likely it is that you make a mistake over time.

And having to trust a third party for privacy is a mistake in the first place IMO. 
 There are few privacy enabling tools that actually work that don't need TOR to function. Monero is probably the only one I am aware of because of dandelion. 
 FYI Dandelion only protects you from other nodes that are communicating and only if you are running your own node. It doesn't protect you from your ISP. So, you still need Tor/Proxies/VPNs/Mixnets to protect you from your ISP and/or if you're using a remote node 
 So it doesn't use encryption to relay the transaction until the dandelion decides to make it public? 
 So this is how I understand it. Hopefully I can explain it correctly.

Everything is still encrypted like normal of course. Dandelion only protects you from malicious nodes on the network knowing what node broadcasted a transaction.

But your ISP would still know you were the one who broadcasted a transaction (they still wouldn't be able to see amounts/receivers). Does that make sense? 
 Damn. Is there a way to get monero running in start9? We need that. 
 Not sure, but all you have to do to protect yourself from your ISP is use Tor or at least a good VPN. But even if you didn't, all they would know is you used Monero. They wouldn't know how much Monero you sent or who received it. 
 It's already there

https://marketplace.start9.com/monerod 
 Good to know 
 Start9 will run monerod over TOR and is setup using the community marketplace. You then connect your client to your start9 server. 

https://github.com/kn0wmad/monerod-startos/blob/master/docs/guides.md/monero-gui.md