So, I thought I'd give an update to my situation. See, once upon a time, I had taken out a trial subscription to a bunch of newspapers. There was no easy way to delete the issues so they stuck around in my account even after I had unsubscribed to them. I had noticed that the kobo software got stuck on those newspapers. For some reason, it would always try to load those issues. After a few calls to get the people at Kobo to delete the issues from my account, I can now sync and connect to my network without issue.
I thought I'd throw this out there in case this might help anyone else having the same issue. Also, as a further recommendation to the kobo devs, can you make it easier to delete old newspaper issues?
tl;dr Issue is resolved. It was due to corrupted newspapers on my account.