are you using a proxy on your windows 2008?
hey imopya
i got running some windows 2k8 servers too
try to add pokefarmer.exe to the enhanced firewall settings.... i think thats the point there
enable your firewall and set exception for PF
INFO <b><font color="#0094FF">[04:07:29]</font></b> Connecting to login servers...
INFO <b><font color="#0094FF">[04:07:30]</font></b> Connecting to game servers...
DEBUG <b><font color="#0094FF">[04:07:30]</font></b> Requesting round #(1)
DEBUG <b><font color="#0094FF">[04:07:31]</font></b> Endpoint changed to pgorelease.nianticlabs.com/plfe/332
DEBUG <b><font color="#0094FF">[04:07:32]</font></b> Endpoint changed to pgorelease.nianticlabs.com/plfe/332
DEBUG <b><font color="#0094FF">[04:07:40]</font></b> Received item templates with timestamp 1481929258150
INFO <b><font color="#0094FF">[04:07:40]</font></b> Connection established.
DEBUG <b><font color="#0094FF">[04:07:40]</font></b> Start Location: 1.3249, 103.749 (0m distance)
DEBUG <b><font color="#0094FF">[04:07:40]</font></b> Start Location: 1.3249, 103.749 (0m distance)
DEBUG <b><font color="#0094FF">[04:07:40]</font></b> Start Location: 1.3249, 103.749 (0m distance)
DEBUG <b><font color="#0094FF">[04:07:40]</font></b> Start Location: 1.3249, 103.749 (0m distance)
DEBUG <b><font color="#0094FF">[04:07:40]</font></b> Start Location: 1.3249, 103.749 (0m distance)
DEBUG <b><font color="#0094FF">[04:07:40]</font></b> Start Location: 1.3249, 103.749 (0m distance)
DEBUG <b><font color="#0094FF">[04:07:40]</font></b> Start Location: 1.3249, 103.749 (0m distance)
DEBUG <b><font color="#0094FF">[04:07:40]</font></b> Start Location: 1.3249, 103.749 (0m distance)
DEBUG <b><font color="#0094FF">[04:07:40]</font></b> Start Location: 1.3249, 103.749 (0m distance)
DEBUG <b><font color="#0094FF">[04:07:40]</font></b> Start Location: 1.3249, 103.749
INFO <b><font color="#0094FF">[04:07:40]</font></b> Next pause at pokestop is in 29 minutes...
INFO <b><font color="#0094FF">[04:07:40]</font></b> Started
INFO <b><font color="#0094FF">[04:11:44]</font></b> Connecting to login servers...
INFO <b><font color="#0094FF">[04:11:45]</font></b> Connecting to game servers...
DEBUG <b><font color="#0094FF">[04:11:45]</font></b> Requesting round #(1)
DEBUG <b><font color="#0094FF">[04:11:45]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:46]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:47]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:47]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:49]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:49]</font></b> Request 2 failed. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:49]</font></b> Requesting round #(2)
DEBUG <b><font color="#0094FF">[04:11:50]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:51]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:52]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:52]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:53]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:53]</font></b> Request 2 failed. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:53]</font></b> Requesting round #(3)
DEBUG <b><font color="#0094FF">[04:11:54]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:55]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:56]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:57]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:58]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:58]</font></b> Request 2 failed. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:58]</font></b> Requesting round #(4)
DEBUG <b><font color="#0094FF">[04:11:59]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:11:59]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:12:00]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:12:00]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:12:01]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:12:01]</font></b> Request 2 failed. Last status was 0.
DEBUG <b><font color="#0094FF">[04:12:01]</font></b> Requesting round #(5)
DEBUG <b><font color="#0094FF">[04:12:02]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:12:03]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:12:03]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:12:04]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:12:05]</font></b> Try request 2 again. Last status was 0.
DEBUG <b><font color="#0094FF">[04:12:05]</font></b> Request 2 failed. Last status was 0.
INFO <b><font color="#0094FF">[04:12:05]</font></b> Could not connect to game servers. Please try again later.
It means you can't connect to the game servers. Are you using proxies or VPN can you switch them off.
So are you still facing issues?
Still have. Not solved yet.
I moved the Pokefarmer to another PC in windows 7. It works very well.