You just can't know-it-all not having experienced it, so reading tips from others would be the next best for sure. That is for safety of the driver, jumper as well as sailors being assisted.

I totally forgot the time in San Felipe when I pulled the rig off my 16 when upside down. The mast was bouncing on the bottom (50 knots off-shore storm / Chubasco hit Midwinters West one year). We couldn't right due to water in the mast. Taking the sail down and pulling the rig off was the last straw. Even a passing Panga couldn't help us. They could have if the rig was still on. After about 6 hours, we were hoisted onto a shrimp trawler by a crane.