Be careful with the firmware. It bricks easily (and no one has provided an unbrick method yet!), even with the files from iriver. My recommendation is to only update it through the wifi updater, which is of course a problem in your case.
As long as it sees the wifi (shows you a list of available networks w/o asking you to enter anything besides the password), that at least means that wifi must be working to some degree; so at least you weren't sold a basic Story HD Basic that has no Wifi at all.
Encryption should not be a problem (wpapsk2 in my case).
You could open the device (4 screws, 2 in the SD slot and 2 hidden under glued-on rubber feet and see if the antenna is connected properly. There is a "story hd teardown" video on YouTube which shows what it's supposed to look like.
Can't speak for Google functionality - never used it.
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I have rooted several android devices and such.
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Well, I've rooted the Story HD (and bricked one in the process), you can find some simple mods here, but none help with wifi issues. Without wifi you can make it run sh scripts as root on startup. However debugging wifi issues this way will be a bit... futile? I don't know.
Some background info used to be here but that site is apparently in the process of dying:
http://morgue.openinkpot.org/wiki/Device/StoryHD