I am familiar with the rig. I built and sail an engineless gaff-rigged Wylo II 35' centerboarder. I crossed the Atlantic 3 times in it with small kids and wife. I have a main topsail on a 17' yard and have no problem setting it up and retrieving it alone. I don't foresee any problem with a much smaller one.
If you google Wylo II you will realize that my dream daysailer looks quite similar to the Wylo II! The Wylo II is my ideal cruiser but it's not a daysailer.
As I mentionned in post 37 I just trailer the boat twice a year.