My Kobo Aura HD, and the wife's Glo had the same problem, after a reboot they connect succesfully, but when they've gone to sleep, they won't reconnect at all, until the next reboot. We only had this problem after updating to firmware 3.0+, the 2.10 firmware and earlier didn't have any problems connecting. Our router is a Fritz!box 7360, a Speedtouch 780 worked though.
As zweiundachtzig mentioned, some users of the German forum lesen.net had the same issue, and they offered the tip to set up DHCP on the router in such a way that it assigns the same IP address to the Kobo's every time. That solved the problem with our router! I feel it should work with a non-fixed IP address, and it actually did before the 3.0 upgrade, so it's a bit of a work-around, but it's working for us.
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