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Emerald Necklace is a nice facility with great staff. Live music there on Friday nights is a good way to end the week. I continue to disagree with management decisions, but on balance I like it there.
Billing for the following season is 100% up-front. A 50% deposit seems like it should be sufficient, with the remaining 50% to be paid at the start of the season. I would also lobby for extending the sailing season. There is still beautiful sailing weather in mid October. I have sailed elsewhere until the end of November.