Sorry for the late reply,
I've been trying to reproduce this issue on a second gameserver but seem to be unable to (even though its hosted on the same virtual machine).
However I just noticed the issue still happens on my initial gameserver which is running latest version of cs:go and latest sp build (Build #265).
Plugins: found file "source-python.vdf"
[Source.Python] Loading...
[Source.Python] Connecting interfaces...
[Source.Python] Retrieving engine interfaces...
[Source.Python] Interface VEngineServer023 at 15fc3c0
[Source.Python] Interface GAMEEVENTSMANAGER002 at 163fbe0
[Source.Python] Interface ISERVERPLUGINHELPERS001 at 167dc20
[Source.Python] Interface EngineTraceServer004 at 163f7e0
[Source.Python] Interface IEngineSoundServer003 at 163f4e8
[Source.Python] Interface VEngineRandom001 at 15fc0d0
[Source.Python] Interface VFileSystem017 at 54d980
[Source.Python] Interface VEngineServerStringTable001 at 164d940
[Source.Python] Interface VPhysics031 at 29cdba0
[Source.Python] Interface VPhysicsCollision007 at 29cdce0
[Source.Python] Interface VPhysicsSurfaceProps001 at 29ce2a0
[Source.Python] Interface MDLCache004 at 9290e0
[Source.Python] Interface VoiceServer002 at 15fc3c4
[Source.Python] Retrieving game interfaces...
[Source.Python] Interface PlayerInfoManager002 at 3b30f28
[Source.Python] Interface BotManager001 at 3b30f24
[Source.Python] Interface ServerGameDLL005 at 3c5c0f8
[Source.Python] Interface VSERVERTOOLS001 at 3b0d904
[Source.Python] Retrieving global variables...
[Source.Python] Initializing mathlib...
[Source.Python] Initializing server and say commands...
[Source.Python] Initializing python...
[Source.Python] Python home path set to /home/ogp_agent/OGP_User_Files/48/csgo/addons/source-python/Python3
[Source.Python] Python version 3.4.1 (default, Sep 3 2014, 21:28:20)
[GCC 4.4.5] initialized!
[Source.Python] Setting sys.argv...
[Source.Python] Adding /home/ogp_agent/OGP_User_Files/48/csgo/addons/source-python/packages/source-python to path
[Source.Python] Adding /home/ogp_agent/OGP_User_Files/48/csgo/addons/source-python/Python3/plat-linux to path
[Source.Python] Adding /home/ogp_agent/OGP_User_Files/48/csgo/addons/source-python/Python3/lib-dynload to path
[Source.Python] Adding /home/ogp_agent/OGP_User_Files/48/csgo/addons/source-python/packages/site-packages to path
[Source.Python] Adding /home/ogp_agent/OGP_User_Files/48/csgo/addons/source-python/packages/custom to path
[Source.Python] Adding /home/ogp_agent/OGP_User_Files/48/csgo/addons/source-python/plugins to path
[Source.Python] Initializing _memory module
[Source.Python] Initializing _bitbuffers module
[Source.Python] Initializing _colors module
[Source.Python] Initializing _commands._client module
[Source.Python] Initializing _commands module
[Source.Python] Initializing _commands._say module
[Source.Python] Initializing _commands._server module
[Source.Python] Initializing _cvars module
[Source.Python] Initializing _effects module
[Source.Python] Initializing _effects._base module
[Source.Python] Initializing _effects._constants module
[Source.Python] Initializing _engines module
[Source.Python] Initializing _engines._server module
[Source.Python] Initializing _engines._sound module
[Source.Python] Initializing _engines._trace module
[Source.Python] Initializing _entities._constants module
[Source.Python] Initializing _entities._helpers module
[Source.Python] Initializing _entities module
[Source.Python] Initializing _entities._factories module
[Source.Python] Initializing _entities._datamaps module
[Source.Python] Initializing _entities._props module
[Source.Python] Initializing _entities._entity module
[Source.Python] Initializing _core module
[Source.Python] Initializing _events module
[Source.Python] Initializing _globals module
[Source.Python] Initializing _keyvalues module
[Source.Python] Initializing _listeners module
[Source.Python] Initializing _mathlib module
[Source.Python] Initializing _messages module
[Source.Python] Initializing _net_channel module
[Source.Python] Initializing _players._bots module
[Source.Python] Initializing _players._constants module
[Source.Python] Initializing _players._helpers module
[Source.Python] Initializing _players module
[Source.Python] Initializing _players._voice module
[Source.Python] Initializing _filters._recipients module
[Source.Python] Initializing _steam module
[Source.Python] Initializing _stringtables module
[Source.Python] Initializing _studio module
[Source.Python] Initializing _studio._constants module
[Source.Python] Initializing _studio._cache module
[Source.Python] Initializing _weapons._constants module
[Source.Python] Initializing _weapons._scripts module
[Source.Python] Loading main module...
[Source.Python] Failed to load the main module.
[Source.Python] Could not initialize python.
Failed to load plugin "addons/source-python"
[Source.Python] Unloading...
[Source.Python] Unhooking all functions...
[Source.Python] Shutting down python...
[Source.Python] Unloading main module...
[Source.Python] Failed to unload the main module.
[Source.Python] Clearing all commands...
[Source.Python] Unregistering ConVar...
[Source.Python] Disconnecting interfaces...
[Source.Python] Resetting cache notifier...
[Source.Python] Unloaded successfully.
Perhaps I should just re-install the gameserver entirely?