Re: Roller reefing
It's definitely crucial to keep some back tension on the furling line as you unfurl. If you let the wind freely roll the sail out you're almost guaranteed to get an override on the drum, possibly unawares until you try to refurl it.
There really shouldn't be any situation (with the possible exception of trying to furl in a real breeze out of the lee of the main - not a good idea in any event...) where you'll need a winch to get the sail to furl.
Unless it's really light air we tend to bear off, get the headsail luffing in the lee of the main sail, control the roll tension with the sheet, then come up to course if necessary.. easier on the hands, the crew and the gear.
Also, when you've got minimal line on the drum an overtight furl can mean you'll run out of line before the sail is fully furled, leaving some sail exposed which can complicate docking and mooring...
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)