I cannot find any hard “Permission Denied” errors in your logs.
What I do see, are networking changes of the VM guest (the OS your server runs in)
The networking replies indicate you have two layers of NAT. One at the ISP/edge and one in the VM. Is this expected? If so then safe to ignore.
I did see an incomplete TLS handshake & Cert setup due to version. This wouldn’t make media unavailable if it’s part of the greater networking changes also occurring.
Aug 11, 2020 17:27:30.071 [0x7fbfe96bb700] DEBUG - HTTP 200 response from GET https://70-118-224-133.a83ce8d56b6f4a469034f8a11592f7c8.plex.direct:8888/identity
Aug 11, 2020 17:27:30.072 [0x7fbfe96bb700] DEBUG - MyPlex: mapping state set to 'Mapped - Not Published'.
Aug 11, 2020 17:27:30.072 [0x7fbfe96bb700] DEBUG - MyPlex: Last published value didn't change, we're done.
Aug 11, 2020 17:27:30.072 [0x7fbfe8eba700] DEBUG - Completed: [192.168.30.1:35086] 200 GET /identity (2 live) TLS GZIP 2ms 451 bytes
Aug 11, 2020 17:41:58.564 [0x7fbfe3fff700] DEBUG - CERT: incomplete TLS handshake: wrong version number
Aug 11, 2020 17:57:05.534 [0x7fbfe96bb700] DEBUG - Sync: uploadStatus
Aug 11, 2020 18:00:12.231 [0x7fbfe96bb700] DEBUG - Statistics: Flushing 1 expired bandwidth entries, 0 expired media entries.
Aug 11, 2020 18:27:05.534 [0x7fbfc5ffb700] DEBUG - Sync: uploadStatus
Aug 11, 2020 18:27:15.088 [0x7fbfc5ffb700] DEBUG - PublicAddressManager: Obtaining public address and mapping port.
Aug 11, 2020 18:27:15.088 [0x7fbfc5ffb700] DEBUG - PublicAddressManager: Obtaining public IP.
In particular, the networking changes appear to be periodic as if a DHCP server is firing / renewing.
Aug 12, 2020 09:27:33.791 [0x7fbfe1ffb700] DEBUG - MyPlex: Last published value didn't change, we're done.
Aug 12, 2020 09:57:05.543 [0x7fbfe1ffb700] DEBUG - Sync: uploadStatus
Aug 12, 2020 10:00:16.204 [0x7fbfe1ffb700] DEBUG - Statistics: Flushing 1 expired bandwidth entries, 0 expired media entries.
Aug 12, 2020 10:14:48.386 [0x7fbfc6ffd700] DEBUG - NetworkInterface: received Netlink message len=88, type=RTM_DELADDR, flags=0x0
Aug 12, 2020 10:14:48.386 [0x7fbfc6ffd700] DEBUG - NetworkInterface: Netlink address message family=2, index=2, flags=0x0
Aug 12, 2020 10:14:48.386 [0x7fbfc6ffd700] DEBUG - Network change.
Aug 12, 2020 10:14:48.386 [0x7fbfc6ffd700] DEBUG - NetworkInterface: Notified of network changed (force=0)
Aug 12, 2020 10:14:48.387 [0x7fbfc6ffd700] DEBUG - Network change notification but nothing changed.
Aug 12, 2020 10:14:48.539 [0x7fbfc6ffd700] DEBUG - NetworkInterface: received Netlink message len=88, type=RTM_DELADDR, flags=0x0
Aug 12, 2020 10:14:48.539 [0x7fbfc6ffd700] DEBUG - NetworkInterface: Netlink address message family=2, index=2, flags=0x0
Aug 12, 2020 10:14:48.539 [0x7fbfc6ffd700] DEBUG - Network change.
Aug 12, 2020 10:14:48.539 [0x7fbfc6ffd700] DEBUG - NetworkInterface: Notified of network changed (force=0)
Aug 12, 2020 10:14:48.540 [0x7fbfc6ffd700] DEBUG - Network change notification but nothing changed.
Aug 12, 2020 10:27:05.543 [0x7fbfe96bb700] DEBUG - Sync: uploadStatus
Aug 12, 2020 10:27:20.740 [0x7fbfe1ffb700] DEBUG - PublicAddressManager: Obtaining public address and mapping port.
Aug 12, 2020 10:27:20.740 [0x7fbfe1ffb700] DEBUG - PublicAddressManager: Obtaining public IP.
Aug 12, 2020 10:27:20.740 [0x7fbfe1ffb700] DEBUG - HTTP requesting GET http://plex.tv/pms/:/ip
Aug 12, 2020 10:27:21.161 [0x7fbfe1ffb700] DEBUG - HTTP 200 response from GET http://plex.tv/pms/:/ip
Aug 12, 2020 10:27:21.161 [0x7fbfe1ffb700] DEBUG - PublicAddressManager: Got public IP from http://plex.tv: 70.118.224.133
Aug 12, 2020 10:27:35.336 [0x7fbfe1ffb700] DEBUG - NAT: UPnP, not an IGD: <http://[fe80::244e:f18e:eb6:2a1]:8096/dlna/f8ee54c322bb4da087904257a90d4471/description.xml>.
Aug 12, 2020 10:27:35.336 [0x7fbfe1ffb700] DEBUG - NAT: UPnP, not an IGD: <http://[fe80::244e:f18e:eb6:2a1]:8096/dlna/f8ee54c322bb4da087904257a90d4471/description.xml>.
Aug 12, 2020 10:27:35.336 [0x7fbfe1ffb700] DEBUG - NAT: UPnP, not an IGD: <http://[fe80::244e:f18e:eb6:2a1]:8096/dlna/f8ee54c322bb4da087904257a90d4471/description.xml>.
Aug 12, 2020 10:27:35.339 [0x7fbfe1ffb700] DEBUG - NAT: UPnP, found device <http://192.168.30.14:8096/dlna/f8ee54c322bb4da087904257a90d4471/description.xml> with private address <192.168.30.18>
Aug 12, 2020 10:27:35.339 [0x7fbfe1ffb700] DEBUG - NAT: UPnP, not an IGD: <http://192.168.30.14:8096/dlna/f8ee54c322bb4da087904257a90d4471/description.xml>.
Aug 12, 2020 10:27:35.342 [0x7fbfe1ffb700] DEBUG - NAT: UPnP, found device <http://192.168.30.14:8096/dlna/f8ee54c322bb4da087904257a90d4471/description.xml> with private address <192.168.30.18>
Aug 12, 2020 10:27:35.342 [0x7fbfe1ffb700] DEBUG - NAT: UPnP, not an IGD: <http://192.168.30.14:8096/dlna/f8ee54c322bb4da087904257a90d4471/description.xml>.
Aug 12, 2020 10:27:35.344 [0x7fbfe1ffb700] DEBUG - NAT: UPnP, found device <http://192.168.30.14:8096/dlna/f8ee54c322bb4da087904257a90d4471/description.xml> with private address <192.168.30.18>
Aug 12, 2020 10:27:35.344 [0x7fbfe1ffb700] DEBUG - NAT: UPnP, not an IGD: <http://192.168.30.14:8096/dlna/f8ee54c322bb4da087904257a90d4471/description.xml>.
Aug 12, 2020 10:27:35.344 [0x7fbfe1ffb700] DEBUG - NAT: UPnP, getPublicIP didn't find usable IGD.
Aug 12, 2020 10:27:35.595 [0x7fbfe1ffb700] WARN - NAT: PMP, got an error: Not Supported by gateway.
I wouldn’t expect DHCP to renew so quickly so therefore wonder if there’s something in the network , outside the VM, which is not being seen.
Does any of this make sense?