Cat 27 limits
Jason, the limit to far over you can heel a Cat27 is only limited by how far it will go before it takes water over the coaming, and ships it down below. reliatically, though, you want to keep the boat moving well, which it's not doing at that angle. The point at which I begin to feel uncomfortable (but not endangered) is when the rail is in the water. At that point it's still moving, but is overpowered and a reducing sail is in order if it's not just a quick gust. And how much to knock down also depends at least in part on how much sail you have up. The old advice is Reef early and reef deep; reef as soon as you first think about it. I've had my 27 double-reefed, 90% jib, beating into 30+ knots, 10-12 ft seas for about 10 hours. We were heeled maybe 20 degrees, 25 on occasion. It was uncomfortable, but we were safe and relatively dry. (I have a dodger).