We experience this commonly on the West River during Tuesday evening racing (A-Cats, single-handed F16s,and double handed N20s). Common practice is to avoid the situation. If it is close, it is not worth getting challenged into a precarious point of sail because the overtaking windward boat has very limited rights and can be "luffed". Ironically, it does not have to be exclusive to sloop vs spin boats. The F16s sail higher than the N20s with the chute.