Re: Help what sail to raise 1st?
Most any boat will tend to 'weathercock' upwind if the aft most sail is raised first.. this is much preferred to having a forward sail up alone that will, if filled or backwinded, wear the boat around and into a probable gybe while you're struggling to raise the aft sail second.
Trying to raise or lower a mainsail in any position other than head-to-wind will make it much harder as the partially raised sail will tend to plaster itself onto the spreaders and shrouds, adding drag and causing chafe, possibly catching and tearing a batten pocket as well.
1984 Fast/Nicholson 345 "FastForward"
".. there is much you could do at sea with common sense.. and very little you could do without it.."
Capt G E Ericson (from "The Cruel Sea" by Nicholas Monsarrat)