How come Shigure and Yuudachi are regularly paired together, is there some sort of historical context for this?

Same artist, same design and the fact that both have Kai 2 and have great stats at certain parts, Yuu being high firepower and Shigure being high anti-air.

If we go by historically, then Shigure should be paired with Shiratsuyu regularly.

It's the power of the Kai-2 hair!