C'Pete,
If you are going to do any serious amount of drillling on stainless you need to regring your drill bit point to be "flatter" than the stock kind. I fergit the exact angle, but the regular bit is too "pointy" for stainless, and will get too hot and just stop cutting. And yes, they need to spin clockwise. Done that myself - yikes, are we getting that old? My wife labels my shoes TGIF - toes-go-in-first.....
I too have been thinkin' hard about moving my halyards aft on my Ariel, but I just may install a tiller pilot instead and keep everything on the mast. Still have some time, it's nasty outside!