This is our 16th charter since 1985, all have been July and August. As with Calsail, only got chased out once and that was the first charter. We love this time of year. Two trips ago we had a depression forming, and after watching it for several days BVIYC advised us to return to base. We were given permission to go to VGYH instead. Spent a two days there then continued our charter.
With the improvements in weather forecasting and communication you will have ample notice if something is brewing. I recall a few years ago the people who went in May had non stop wind and rain for days on end.
We do trip insurance because we have elderly parents here at home and because we are no longer spring chickens ourselves.