Roller Furling is convenient and adds an element of safety as you don't have to go forward to unhank the headsail, fold it and bag it - which can be especially dangerous if in high winds and big seas. With the sail easily furled you eliminate the need to stow a bagged sail somewhere in the cabin (takes up room in the living area of your boat), or perhaps the cockpit locker. There are several manufacturers to choose from and you should consider your budget and how you use the boat. If you often raise and lower your mast traveling to different bodies of water to enjoy, then you might want to pick a furler with a flexible extrusion. The two basic types that come to mind are the CDI (Cruising Design Inc - now owned by a Canadian company) and Schaefer's Snap Furl. The CDI uses it's own halyard system while the Snap Furl uses your existing halyards. If you have more than one head sail, like a racer might have, then you will better be served with the Snap Furl. Otherwise, the CDI is cheaper. Both are easy to install. If you have a bigger budget and your boat sits with the mast up all summer, then you might consider a more sophisticated system like Furlex (Selden) or Harken. As far as sail modification is concerned, you have to have the hanks removed as mentioned before and a luff tape installed to fit the slot in the system you choose. In addition, the hoist of the leading edge of the sail may have to be shortened to accommodate the drum at the bottom and a swivel at the top, if the system uses one (CDI doesn't). For better headsail shape when the sail is partially furled, you would want a foam or rope luff (depends on the sailmaker) as that will help develop better draft. If you just have a luff tape without the foam or rope luff, the sail will be very flat midway for reefing. I believe CDI is not recommended for partial furling, but the Snap Furl is as are more expensive systems. Also, since your headsail will be wrapped around your forestay/extrusion, a sacrificial cloth should be added to the luff and foot of the sail to protect the sail cloth from sun degradation. It is easier and cheaper to remove old UV material and add new stuff than replace the entire sail. If you have a very old sail that isn't worth much, it doesn't make sense to spend a bunch of money on it to accommodate the furling modification. You will be much happier with a new sail, designed and built for furling and made to fit the system that you choose.