Ahoy Aaron,
If your winches are mounted right on the mast, either someone didn't worry much about the fit or the section is flat or maybe the winches are up on a sort of rail like lift. The latter is good but you can't get the lead you want, which I don't recommend anyway but that's coming below.
The winch should have a pad of a durable molded in place plastic (I like MarineTex for this) or, I feel better, wood. A really fast way to get the fit is to rough out the hollow with a chisel, then hold some coarse (40# to 60# sandpaper on the mast and rub the hollow smooth. It's quick and easy and makes a fit good enough that you'll only need a little bedding compound under the pad and under the winch.
As to the lead, if you cock the winch down to make the lead as you might properly cock a sheet winch horizontally out, you make a situation where the winch handle can fall out more readily (even with a lock) but more importantly where your hold for grinding is actually harder to use.
I like my winches dead normal to the mast. I hoist most of the way just hauling and pop a wrap on when I'm within a few feet of the truck. It's easier to pull down, using some weight. But so long as you're hauling and not grinding, at least have only one turn on the winch. It's almost impossible to get a wrap with but one turn. Add the other two turns for grinding only when you're about to stick the handle in and grind.
It's pleasing that the convention of halyards controlling sails forward of the mast (jibs, staysails, etc.) are to port while sails set abaft the mast (mains, mizzens, foresails) are to starboard has survived to modern boats. At least for the right-handed majority. When you get to grinding, the natural stance lets you crank with the right hand, tail with the left, and hold a stance that gives a view of the sail in question.
G'luck
Ian
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