Did the Jalapeno 100 with my wife, her on SS me on FG, while pulling 3 children in two trailers. My oldest son rode a 24" road bike for the first time (in a group). Winds were 30 MPH from the NNW with a 20 degree temp drop right as we set out. Was fun as hell watching my wife pedal into the wind for the first time, get to the turn around and get all happy. Was fall on the ground hilarious when she realized that "looping back" meant riding directly into those same winds that were crosswinds on the way out. She immediately suggested mounting a motor on the trailer.
She did well, we all survived her vulgarity fest. Next challenge will be to get her to flip her wheel over to the fixed cog since she never got to coast in the first place.