Charging in the rain/snow

There are a lot more potential mechanical issues with snow or freezing rain, but I can say for the soggy but not-so-cold Pacific Northwest, where we get spectacular amounts of rain that never freezes, I've been charging my cars outdoors and unprotected for years without issue. The J1772 interface does not energize the power until it has confirmed a connection to a car, and the pins are extremely deep for a reason. Plus there's a delay of a few seconds and fault detection, so you will probably have let go before charging starts, at which point a short (if the connector were completely drenched and had an electrical path where one shouldn't exist) would be detected and shut down charging.

The only thing I'd really be worried about would be water inside the connector corroding the metal contacts.