I agree, PirateWeather seems like a misbrand here. When I read it, i thought it was stealing weather data or something. On the web, the term "pirate" generally doesn't mean good things. This name almost implies that it is illegal or something.

I'm imagining designing a software product around this and presenting it to a C-Level, explaining that we use "PirateWeather" and I think I'm going to get grilled with lots of questions and concerns based on the name alone.

This is a good service and should be "branded" with a better name. Maybe a play on the whole DarkSky name like LightSky or "Sunset" which works exceptionally well since DarkSky was sunset by Apple. Maybe StarrySky, LateSky, NewSky.

I am usually someone who says that names don't matter as much as people think they do, but PirateWeather just seems like a huge hit in the wrong direction. But the product is solid so maybe it can survive despite the name.