From a 99 Owner- some perspectives
As a C&C 99 owner for the last 8.5 y, I can say we have been very satisfied with the boat. We race on the Chesapeake and find the boat, when well sailed, with a coordinated crew, to be competitive in 1 design. PHRF out here is 108.
As to your question regarding reefing, we use a medium 150% #1 up to about 12 kn true. After that we switch to a heavy #2 (135%) , which we can carry up to ~ 18+ kn true. At that point, we can reef the main (1 point) or switch to a 100% #3. The key to decent boat speed in the 99 is to keep the boat somewhat flat. Heel angles above 20 degrees mean the boat begins to lose forward velocity a bit. Crack off the main or put some good twist in the top and that often solves the immediate problem.
One thing that is very cool in these boats is that the steering is basically 1:1. The rudder goes lock to lock in one turn of the wheel. Means steering is very sensitive. Also means that with weather helm, it takes some force to track the boat, especially in waves. However, reduce helm by dropping the traveler or twisting off the top of the main and the sensitivity is a real plus. On the race course, the boat is significantly more agile than others of the same length...even tiller boats (usually because they have smaller rudders).
The Volvo sail drive has performed very well for us. We had some issues with he water integrity of the ignition circuitry but have fixed those problems. At 3000 RPM with a 2 blade folding Volvo prop, we can get ~ 6.5 - 6.8 kn in flat water with no current. Maneuverability is fantastic although with any saildrive you need to make sternway to get steerage, since the rudder is located about 5-6 feet aft of the propeller. Prop walk is minimal at best. Basically, the boat
The cockpit is a bit small for a full racing crew. We regularly race with 7 in order to run a full kite. Upwind speeds are usually ~ 6.5 - 6.8 kn.
We have also cruised our boat a bit. Although the manufacturer says it sleeps 6, I think it is better suited for 2...4 in a pinch. Black water tankage is a bit small, but that also means dead weight in the bow is kept lower, too.
For its price, depending on your sailing needs, it is a good value for a racer cruiser. It certainly is in many ways a better buy than a new J-105 ( which we often beat in racing here in the Chesapeake), which lists I believe at over $200K and is not really conducive to any cruising if desired. The key of course is to sail it well.
Another advantage i enjoy is the ability to easily single hand the boat. The large primary winches back at the helm allow this.
Hope this helps.