Very risky to put in at Rollover and run to Joseph's Harbor entrance. 15 miles. My uncle and I capsized a 20' aluminum boat trying to do just that. 20 mile hour South-Southeast wind. That beach is very unfriendly on a stiff south wind.
I will tell you this. During the summer you get a predominantly Southwest wind. Normally the mornings are calm. If you can make it to Joseph's Harbor in the morning on the lite surf you can go back to Rollover with the swell. You don't want to be going into the waves on the beach, always with them.
You also don't want to leave the mouth of rollover with a stiff south wind and an outgoing tide. The waves stack at the entrance where the tide meets the wave. It makes for tall waves close together. That combination is a killer of boats.
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