I tried the trick of manually slowing down the GS108T port to 100/half duplex as posted elsewhere, no luck there.
I toted the OBi upstairs and plugged in to another access point, a NetGear WN604 and it worked just fine there.
I took the OBi to the office and plugged it in to a NetGear GS748T managed switch and it worked just fine there too.
I will recheck the WRT54G but I am pretty sure its not double NATed as I can see all the game stations plugged in to it when I scan with AngryIP and have never had any conflict issues. It only has gaming stations attached, no other switches or anything.
The RT-N66 is the only device handing out IP addresses unless I got something screwed up but I don't think so.
The GS108T and the WRT54G are wired straight to the RT-N66 but the NetGear WN604 is connected through another unmanaged switch (a trendNet gigabit?) in the garage attic so that rules out the switch causing issues since the WN604 worked for me.
I am leaning towards the GS108T not playing well with the OBi 200 for some reason. I do find it a strange coincidence that someone else posted issues with the same exact model. I will do a factory reset on it today and see if that changes anything, but I don't recall changing any settings until today when I manually changed the port speed on the OBi's port.
I will also unplug all the cables from the RT-N66 except the one going to the GS108T and see it that changes anything. I can draw up the network map and post that if you want, but unhooking all the cables but one should rule out any double NAT possibilities.