Device not responding

"The reason the first ping usually fails is that the remote router in that LAN has to put the ping request on hold to send out an ARP broadcast to learn the MAC address of the remote device, then wait for a response, and then send the first ping through"

I would look at your router settings....use the info above to find more information on the networking issue and hopeful resolution.

Pings don't fail. The device is disconnecting and then reconnecting. There are Zero network issues going on. All the Home automation stuff (IP smart lights, switches, etc) stays online and are triggered normally.

This is normal...(a bit slower because it is from a wifi laptop)

bitzerj@WINTHINKPADJB:~$ ping 192.168.2.202
PING 192.168.2.202 (192.168.2.202) 56(84) bytes of data.
64 bytes from 192.168.2.202: icmp_seq=1 ttl=99 time=6.17 ms
64 bytes from 192.168.2.202: icmp_seq=2 ttl=99 time=5.93 ms
64 bytes from 192.168.2.202: icmp_seq=3 ttl=99 time=6.70 ms
64 bytes from 192.168.2.202: icmp_seq=4 ttl=99 time=6.07 ms
64 bytes from 192.168.2.202: icmp_seq=5 ttl=99 time=6.24 ms
64 bytes from 192.168.2.202: icmp_seq=6 ttl=99 time=9.18 ms
64 bytes from 192.168.2.202: icmp_seq=7 ttl=99 time=5.49 ms
64 bytes from 192.168.2.202: icmp_seq=8 ttl=99 time=5.84 ms
^C
--- 192.168.2.202 ping statistics ---
8 packets transmitted, 8 received, 0% packet loss, time 7012ms
rtt min/avg/max/mdev = 5.493/6.450/9.175/1.079 ms

We have hundreds / thousands of these IP2IR boxes in systems. I doubt it's the GC.
You can ping the GC and the first / second / third ping are all less than 5ms response? If not, then you may have a networking problem.
Edit:  The ping times you are providing all are more than 5ms.  That's a somewhat slow network.  All of mine are less than 1ms (including the first).
The driver waits 5s (100X longer) and will post an error if no response in that time.

The ping times are higher than normal because they are from a laptop on Wifi. Here are the pings from the myserver...

allonis@bitzer:~ $ ping 192.168.2.202
PING 192.168.2.202 (192.168.2.202) 56(84) bytes of data.
64 bytes from 192.168.2.202: icmp_seq=1 ttl=100 time=1.00 ms
64 bytes from 192.168.2.202: icmp_seq=2 ttl=100 time=1.05 ms
64 bytes from 192.168.2.202: icmp_seq=3 ttl=100 time=0.987 ms
64 bytes from 192.168.2.202: icmp_seq=4 ttl=100 time=0.938 ms
64 bytes from 192.168.2.202: icmp_seq=5 ttl=100 time=1.06 ms
64 bytes from 192.168.2.202: icmp_seq=6 ttl=100 time=1.01 ms
64 bytes from 192.168.2.202: icmp_seq=7 ttl=100 time=0.899 ms
^C
--- 192.168.2.202 ping statistics ---
7 packets transmitted, 7 received, 0% packet loss, time 6006ms
rtt min/avg/max/mdev = 0.899/0.992/1.061/0.053 ms

My network has been rock solid.... I doubt it is both devices, but something is causing them or the driver to think they become disconnected.

Those pings look better.
But isn't the issue of the first connection after a longer wait of no connection? Can you duplicate that with a ping report?

No, that was a theory... the Wifi pings would show that the first reply back took a bit longer. That doesn't appear to be the case when pinging from the server. I implemented a Static IP in case during the renew it was an issue and implemented a cron job to ping the GC to keep it alive (not needed, that isn't the issue).