That sounds very much very much like the issue that is bugging me for at
least 6 months now - my log Looks quite similar, apart from the file
open issue. 
http://forums.slimdevices.com/showthread.php?107368-LMS-auf-Windows-Server-bleibt-stehen
(sorry, in german and no solution yet)
I'm quite sure it's about connectivity to mysb.com - in your case
because of the VPN, in my case (probably) due to DNS-issues.
Can LMS be made more robust when there are Problems connecting to
mysb.com?

I my case it all started with a LMS 7.9.x nightly I installed mid 2016
IIRC.

Best regards,
Flo


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