I tested again tonight with the Gutsy Tribe-4 i386 live cd and the
results appeared to be the following:

ifup with wpasupplicant works most of the time, I managed to get it to
fail sometimes but not very often. Its usable but can be irritating,
when it decides to fail it usually does it repeatedly.

Network Manager most of the time only sees the open AP and can not
connect to it. For some reason it could not see the WPA AP most of the
time. I also noticed that several times (at least) when the system first
booted it actually would already be connected to the open AP by the time
it finished booting and I ran ifconfig. However NM did not show the
network as connected. I don't know if that was related to why I was not
seeing the WPA AP, perhaps it didn't see it since it was already
connected to the open AP when it did the scan? Also if I tried to
connect to the open AP after it had already connected on boot via NM it
would not connect to the network. Somehow at one point (I don't remember
the details) I was able to get NM to connect (associate) to the open AP
but it did not run dhclient to get an ip address. I was able at that
point to run ifup and it obtained the ip address, I did not have to
change anything in /etc/network/interfaces for that to work apparently
because it was already associated at that point and it seemed to just
run dhclient.

It is possible some of these issues are related to ipw3945 in particular
but the fact that ifup/wpasupplicant works the majority of the time
makes me think it is just NM being extremely buggy.

-- 
[ipw3945] nm fails to connect to open network
https://bugs.launchpad.net/bugs/128360
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