He actually commanded the Queen's Rangers (American Loyalists) who served in the New Jersey campaign and marched on Philadelphia. I infer from that that Simcoe was away from Long Island and didn't have another opportunity to look for Woodhull.
In the show he's a darn good villain. His voice is creepy. Hope that's not how he talks off camera.
It was in Jersey as I recall that Simcoe’s rangers cut down a bunch of rebels guarding (not very well) a ferry pass or some such. Supposedly they recognized each other as neighbors to an extent and greetings were offered but they butchered them all anyway.
The guy is revered up in Niagara. He was a governor or some such; the town has a statue for him.