Yup. Talk to the skiers first. Just head out in the am to chat.
Not sure if the HOA would have jurisdiction on the lake or not. Mich dnr / deq likely does. They would probably issue the permit.
Having HOA support is likely helpful. At best you will probably need to take down by noon on sat and put back up Mondays. Unless the lake owners don't mind and complain if you leave up all the time.
Check ski it again for used courses.