The good news, I realized the problem was in the logs all along. The bad news, your system is not keeping the correct time. Meaning your clock is jumping ahead. Under normal use (no vpn) time sync is able to correct this but using a VPN is compounding this issue.
See how sdwdate
is jumping 1 hour ahead of your OpenVPN logs? But this is happening at the same time.(should both have the same time stamps) Take a look at the rest of your logs and pay attention to the time stamps.
Just to elaborate: Even though sdwdate is set to sleep for 70 minutes try to ignore that when you look at the rest of your logs. I think its pretty clear because Tor can not be fully bootstrapped when your VPN connection is down. Time problem.
Openvpn.log
Sat Nov 24 15:26:13 2018 TUN/TAP device tun0 opened
Sat Nov 24 15:26:13 2018 Note: Cannot set tx queue length on tun0: Operation not permitted (errno=1)
Sat Nov 24 15:26:13 2018 do_ifconfig, tt->did_ifconfig_ipv6_setup=0
Sat Nov 24 15:26:13 2018 /usr/bin/ip_unpriv link set dev tun0 up mtu [redacted]
Sat Nov 24 15:26:13 2018 /usr/bin/ip_unpriv addr add dev tun0 [redacted]/24 broadcast [redacted]
Sat Nov 24 15:26:18 2018 /usr/bin/ip_unpriv route add [redacted]/32 via 10.0.2.2
Sat Nov 24 15:26:18 2018 /usr/bin/ip_unpriv route add 0.0.0.0/1 via [redacted]
Sat Nov 24 15:26:18 2018 /usr/bin/ip_unpriv route add 128.0.0.0/1 via [redacted]
Sat Nov 24 15:26:18 2018 UID set to tunnel
Sat Nov 24 15:26:18 2018 Initialization Sequence Completed
Sat Nov 24 15:30:39 2018 [server] Inactivity timeout (–ping-restart), restarting
Sat Nov 24 15:30:39 2018 SIGUSR1[soft,ping-restart] received, process restarting
Sat Nov 24 15:30:39 2018 Restart pause, 5 second(s)
sdwdate.log
2018-11-24 15:27:49 - sdwdate - INFO - Success. Sleeping for 70 minutes.
2018-11-24 15:27:49 - sdwdate - INFO - Running command: sleep 4200.139213678
2018-11-24 15:27:50 - /usr/bin/whonix-gateway-firewall - OK: Skipping firewall mode detection since already set to ‘full’.
2018-11-24 15:27:50 - /usr/bin/whonix-gateway-firewall - OK: (Full torified network access allowed.)
2018-11-24 15:27:50 - /usr/bin/whonix-gateway-firewall - OK: Whonix firewall loaded.
2018-11-24 16:37:50 - sdwdate - WARNING - Clock got changed by something other than sdwdate. seconds_to_sleep: 4200 time_delta: 4201
2018-11-24 16:37:50 - sdwdate - INFO - Running sdwdate main loop. iteration: 2 / 10000
2018-11-24 16:37:50 - sdwdate - INFO - Running sdwdate main loop. iteration: 2 / 10000
2018-11-24 16:37:50 - sdwdate - INFO - Prerequisite check: The clock is sane.
Within build timestamp Sat May 12 16:21:25 UTC 2018 and expiration timestamp Tue May 17 10:00:00 UTC 2033.
Clock within consensus parameters consensus/valid-after 2018-11-24 14:00:00 and consensus/valid-until 2018-11-24 17:00:00.
2018-11-24 16:37:50 - sdwdate - INFO - Prerequisite check: Tor fully bootstrapped.