There are way more experienced racers on this forum that should be answering this. But, one novice Hunter racer to another, if it’s within 15 degrees of DDW, whisker pole wing on wing. And outside 60 degree close reach to almost DDW, rig outboard jib sheets and a twing. Outboard jib sheets on reaches are worth half a knot even with our small jibs. At about 3:20 in this video from Labor Day weekend, I’m changing to an outboard jib sheet, just after that you see us wing on wing catch and pass a C355 with a big genoa on a short downwind leg. Yeah, it’s the same one that beat us last Saturday, though.