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I'm repeatedly encountering statements related to passive monitoring.

Like that:

If you send XMR frequently to another person, an attacker passively monitoring both parties will know with increasing probability that you have sent XMR to this person. In other words, the probability of someone consistently using your transactions in a ring signature is low. monero wallet packet sniffing

also

For broadcasting own transactions you can probably keep even more privacy when using a hidden node over the i2p network, since you will not disclose your IP address along with your transaction to anybody.
what is a remote-node

I'm thinking, from simple to complex:

  1. Run VPN > Run node behind > XMR wallet > USD-BTC-XMR on one of the exchanges > spent XMR.

No good, the exchange can identify my Monero address along with my passport, etc.

  1. Run VPN > Run node behind > XMR wallet[1] > USD-BTC-XMR on one of the exchanges > XMR to wallet[1] > XMR to [wallet2] > spent XMR.

No good, I guess, small(ish) risk when broadcasting from the same set of IPs.

  1. Run VPN[1] > Run node[1] behind > XMR wallet[1] > USD-BTC-XMR on one of the exchanges > XMR to wallet[1] > Run VPN[2] > Run node[2] behind > XMR to wallet[2] > spent XMR.

Probably, can get away with that, not facing extremely motivated adversary.

Run VPN - actually I'm running OpenVPN over stunnel4 over Whonix(Tor) virtual machine over a router, VPN issues new address for each reconnection (after Tor expires).

Nodes uptime close to 24/7.

Does it make sense to run two nodes in order to disguise identifiable information?

Why is that overkill?

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There is a small amount of metadata leaked if you broadcast transactions from the same IP address. Luckily, if you are using a VPN, you should be safe from the attacker connecting these transactions to your real IP. However, the transactions may still be connected to each other.

To mitigate this risk (which I would consider already very small), you need to break the link between these IP addresses being correlated to each other. It's probably not worth your time to run different nodes for this, but you can connect your node to a different VPN for each transaction you make.

Once Kovri is fully-implemented, then you would no longer need to be concerned about this potential risk.

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