(Let's try this again with out fat fingering the /Send/ button too soon.)
Any idea what's going wrong there? Is there anything I'm overlooking with my routing setup, or do I need to look for the problem on the OSX side?
The first thing that comes to mind is that you may be dealing with an MTU / MSS issue. Some of your connections work and some never seem to start, which is a classic symptom of an MTU / MSS mis-match with the ICMP error being filtered out along the way.
Try playing with the TCPMSS match extension and target to clamp the MSS to some lower values. Try something extremely low and then start raising it until you start to have failures again and then back it down a bit.
PPPoE, despite being nice for providers, has many different problems that simple static IPs or even DHCP does not have.
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