It’s probably not quite as dodgy as it looks / sounds. The fact you have spider webs is a good sign it’s not actually getting wet, as is the fact the fault was with the Networking not the power.
It’s inside an enclosure (which is protecting it effectively) so I don’t think it needs to be full on IP65. Something like IP44 is probably more than adequate (and it may not even need to be rated at all). I’d be more interested in whether the pole itself is effectively grounded? If it is then the scaremongers about it becoming live are just that, and it’s likely the the circuit has trip on it anyway.
The problem with many IP rated socket enclosures is 1. Some are only rated when nothing is plugged into them! 2. Some will only take a standard socket not a 12v style adapter; 3. Those that do might be too big to fit through the opening in the pole.