Well, I thought I had this issue worked out, but my pf rules aren't evaluating as I expected them to:

PF Rules: (rule number prepended, these are the _last_ 6 lines in my pf.conf)

39:pass out quick log on em0 from 172.16.0.1 route-to (em0 192.168.0.1)
40:pass out quick log on em1 from 172.16.1.1 route-to (em1 10.10.0.1)
41:pass out log on em0
42:pass out log on em1
43:pass out log on em0 from em1 route-to (em1 10.10.0.1)
44:pass out log on em1 from em0 route-to (em0 192.168.0.1)



Tests:

$ traceroute -s 172.16.0.1 -n google.com



Tcpdump pflog0 output:

Aug 27 15:35:16.418090 rule 42/(match) pass out on em1: 172.16.0.1.34561>  
74.125.45.106.33438: udp 12
Aug 27 15:50:01.658596 rule 41/(match) pass out on em0: 172.16.0.1.63615>  
74.125.45.103.33444: udp 12



Why are these packets not being caught by rule 39 and always going out the em0 
gateway?

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