Hey Jason…I have a question. If you sail/race with Roo...what DOES happen if you capsize...have you tried it? Roo is tied to the boat, right...what happens if he gets trapped under the sail, or gets wrapped up in some rigging? I've never sailed on a scow but know of the boats and I do understand that they capsize. I ask because I've sailed/raced one design for years (lasers, J24s - owned my own--and crewed for years on PHRF, One Tonners, 50ft class, IMS and MORC (traveling from Maine to Florida for huge regattas both inshore and offshore))...I've seen many unexpected and sometimes bad things happen.
You might want to capsize a few times on purpose with him so that at least you'll know how it goes in a planned situation. Trust me, the man overboard drill I learned and practiced every year came in handy on more than one occasion. Its one thing for a person that knows they need to keep their head up and can figure their way out of being trapped, but I'd be worried that an animal would not know what to do if trapped underwater. I've been trapped underwater under a sail before and trying to get an air pocket under it isn't as easy as you might think and is quite disorienting (as you're pushing up, you are going down)...and I'm a STRONG swimmer.
I'm not trying to be an alarmist, but I would seriously practice the whole thing...and not just once. I've raced on boats with olympic class sailors (in fact, a couple of gold medalists and 2 silver medalists and others who have competed at the olympics). And throughout the years, every one of the boats with these uber experienced people have run into trouble (whether due to weather, boat failure, shifting wind conditions or crew inattentiveness)...things that have happened include flash tacks due to a wind shift, broaches, capsize/pitchpole and mast breakage and people have ended up in the water unexpectedly.
Just something you might want to consider. I always prefer to try things out in a controlled setting and then at least it isn't a complete surprise.