Skipper Dan. The challenge as a boat owner is to decide what is needed and what is eye candy. Your sails are not that heavy to lift by your self, is that correct? If so then you should not need a winch on the mast. Recommend you assure that the luff tracks on the main, and or the jib/genoa are clean and if you want lubed with something like SailKote. (
http://www.mclubemarine.com/sailkote/index.php?c=recapps). So your sail moves smoothly through the track/bolt rope channel.
If you can lift the sail with ease when on the dock you can haul it up the mast with out a winch.
If you want to assure it is to the top and "stretched" run the halyard beneath the mast cleat and pull up (tension the mast halyard) with one hand. Grab the halyard running along the mast and lean back pulling the halyard down and out. Take up any slack you create using the cleat as an aide. The cleat will help to stop any slip. You will be able to tighten the luff enough to put a wrinkle in the sail. Let it off a bit and then tie off on the mast cleat.
I believe the only reason for a winch on the mast is if the sail is heavier then you can lift (pick up and carry) My boat is 35 feet and the sail area is just on the verge of getting too big to handle. So I installed a 17 ST Barient winch on the mast. It allows me to do the work of raising a sail solo. But until I get to old to haul it up I still prefer to haul the sail up by hand. It lets me know if I have a problem aloft before I rip the sail trying to winch it up.
As always it is your boat and you get to decide what to spend your money on.