Well I've ironed out the issues with permissions and I'm relatively confident it is all correct. I think one issue I was experiencing was running the PlexConnect.py file as root. I created a batch file which runs it with administrator permissions (but I was forgetting to run it that way). Regardless, my issue still exists.
To answer your other question - yes I am using Plex Home. I have a PIN and users and all that.
I'm back to being stumped again. No change in results from what I've had all along. And I still don't know why I can't generate a verbose version of the log file.
Settings.cfg
[PlexConnect]
enable_plexgdm = False
ip_pms = 192.168.0.173
port_pms = 32400
enable_dnsserver = True
port_dnsserver = 53
ip_dnsmaster = 8.8.8.8
prevent_atv_update = True
enable_plexconnect_autodetect = True
ip_plexconnect = 0.0.0.0
hosttointercept = trailers.apple.com
port_webserver = 80
enable_webserver_ssl = True
port_ssl = 443
certfile = ./assets/certificates/trailers.pem
allow_gzip_atv = False
allow_gzip_pmslocal = False
allow_gzip_pmsremote = True
loglevel = High
logpath = .
Logfile:
22:18:24 PlexConnect: started: 22:18:24
22:18:24 PlexConnect: Version: 0.5-dev
22:18:24 PlexConnect: Python: 2.7.9 (default, Dec 10 2014, 12:24:55) [MSC v.1500 32 bit (Intel)]
22:18:24 PlexConnect: Host OS: win32
22:18:24 PlexConnect: PILBackgrounds: Is PIL installed? False
22:18:24 Settings: getsetting enable_plexconnect_autodetect=True
22:18:24 PlexConnect: IP_self: 192.168.0.173
22:18:24 Settings: getsetting hosttointercept=trailers.apple.com
22:18:24 Settings: getsetting enable_dnsserver=True
22:18:24 DNSServer: started: 22:18:24
22:18:24 Settings: getsetting port_dnsserver=53
22:18:24 Settings: getsetting ip_dnsmaster=8.8.8.8
22:18:24 Settings: getsetting prevent_atv_update=True
22:18:24 DNSServer: ***
22:18:24 DNSServer: DNSServer: Serving DNS on 192.168.0.173 port 53.
22:18:24 DNSServer: intercept: ['trailers.apple.com'] => 192.168.0.173
22:18:24 DNSServer: restrain: ['mesu.apple.com', 'appldnld.apple.com', 'appldnld.apple.com.edgesuite.net'] => 127.0.0.1
22:18:24 DNSServer: forward other to higher level DNS: 8.8.8.8
22:18:24 DNSServer: ***
22:18:24 Settings: getsetting enable_webserver_ssl=True
22:18:24 WebServer: started: 22:18:24
22:18:24 Settings: getsetting port_webserver=80
22:18:24 WebServer: ***
22:18:24 WebServer: WebServer: Serving HTTP on 192.168.0.173 port 80.
22:18:24 WebServer: ***
22:18:24 WebServer: started: 22:18:24
22:18:24 Settings: getsetting port_ssl=443
22:18:24 Settings: getsetting certfile=./assets/certificates/trailers.pem
22:18:24 Settings: getsetting certfile=./assets/certificates/trailers.pem
22:18:25 WebServer: ***
22:18:25 WebServer: WebServer: Serving HTTPS on 192.168.0.173 port 443.
22:18:25 WebServer: ***
22:21:26 DNSServer: DNS request received!
22:21:26 DNSServer: Source: ('192.168.0.146', 57750)
22:21:26 DNSServer: Domain: www.isg-apple.com.akadns.net
22:21:26 DNSServer: ***forward request
22:21:26 DNSServer: -> DNS response from higher level
22:21:26 DNSServer: DNS request received!
22:21:26 DNSServer: Source: ('192.168.0.146', 54149)
22:21:26 DNSServer: Domain: init.itunes.apple.com
22:21:26 DNSServer: ***forward request
22:21:26 DNSServer: -> DNS response from higher level
22:21:27 DNSServer: DNS request received!
22:21:27 DNSServer: Source: ('192.168.0.146', 52092)
22:21:27 DNSServer: Domain: xp.apple.com
22:21:27 DNSServer: ***forward request
22:21:27 DNSServer: -> DNS response from higher level
22:21:27 DNSServer: DNS request received!
22:21:27 DNSServer: Source: ('192.168.0.146', 62872)
22:21:27 DNSServer: Domain: p2-buy.itunes.apple.com
22:21:27 DNSServer: ***forward request
22:21:27 DNSServer: -> DNS response from higher level
22:21:27 DNSServer: DNS request received!
22:21:27 DNSServer: Source: ('192.168.0.146', 49848)
22:21:27 DNSServer: Domain: mesu.apple.com
22:21:27 DNSServer: ***restrain request
22:21:27 DNSServer: -> DNS response: 192.168.0.173
22:21:28 DNSServer: DNS request received!
22:21:28 DNSServer: Source: ('192.168.0.146', 57750)
22:21:28 DNSServer: Domain: www.apple.com
22:21:28 DNSServer: ***forward request
22:21:28 DNSServer: -> DNS response from higher level
22:21:28 DNSServer: DNS request received!
22:21:28 DNSServer: Source: ('192.168.0.146', 61925)
22:21:28 DNSServer: Domain: apple.com
22:21:28 DNSServer: ***forward request
22:21:28 DNSServer: -> DNS response from higher level
22:21:40 DNSServer: DNS request received!
22:21:40 DNSServer: Source: ('192.168.0.146', 65369)
22:21:40 DNSServer: Domain: trailers.apple.com
22:21:40 DNSServer: ***intercept request
22:21:40 DNSServer: -> DNS response: 192.168.0.173
22:21:42 DNSServer: DNS request received!
22:21:42 DNSServer: Source: ('192.168.0.146', 55879)
22:21:42 DNSServer: Domain: configuration.apple.com
22:21:42 DNSServer: ***forward request
22:21:42 DNSServer: -> DNS response from higher level
22:22:12 PlexConnect: Shutting down.
22:22:12 DNSServer: Shutting down.
22:22:13 WebServer: Shutting down (HTTPS).
22:22:13 WebServer: Shutting down (HTTP).
22:22:13 PlexConnect: shutdown