Re: Not Sure Wich Winch to use
If that is going to be a permanent piece of hardware, you really need to switch it out for a standard block. It looks like you are using a Ronstan 6710 or something in that size range, and they are just not strong enough to handle the loads a turning block will see. It isn't the static loads that will break it, but a shock load from hitting a wave, or when the sail fills suddenly. If I am right about which block that it, it is rated to only about 2000lbs MBS, compare that to a Harken 57mm black magic rated to 3500lbs or a high load block rated to 5000lbs.
Please, please, please go hire a local racer/boat bum to go out with you for an afternoon. Even if they aren't instructors, a lot of the problems you are having just require a few minutes of work from someone who is knowlagable to get you guys in much better shape. At least around here I can grab a local boat guy from a couple of beers, and a promise to take his girlfriend out with us.
If you are in Beaufort SC, in fact just take a walk down to Beaufort yacht club and ask around, you can probably get a couple of guys to help you out for nothing except a promise to go sailing. I am pretty sure there is also a college team that sails out of there, and they could be a good resource for someone that can help you out.
You have a beautiful boat, and it is very well equipped, but poor rigging can not only make sailing more dangerous for you, it can also seriously damage the boat.