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First, I assume you meant those two interfaces to be the same.


No, I didn't. I meant that the local proxy is configured to send its traffic via 'eth1', and that the routing tables cause everything else to go via 'eth0'.

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How do you configure the proxy to send its traffic to a device on a particular interface?


You can't, without either facilities in the hosts TCP/IP stack (which don't exist -- I thought they did), or by using source-routing (which isn't supported).

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and there's not a practical way to figure out how to add such static routes, or to actually add them.


The Windows stack does provide an API to modify the routing tables. I'm not sure how dynamic it is, and I'm unconvinced about having a SOCKS proxy f*ck with the routing table before it makes the outbound connection.
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-- roger