Mike, I did drill through the metal, and the glass lip. I don't think it has caused any structural problems. I also sealed the holes with West System epoxy as I went so water wouldn't seep into the glass. The two jibs, and seperate mountings sound OK, though since the "Super" is roller furling, I don't see the need for the smaller one. I don't recommend taking two adults, since the hulls aren't boyant enough to keep the tramp out of the water unless you are flying a hull, but I have done it several times, and as long as the wind was over 12 knots it was still fun. I still like to sail it solo, as the tramp dragging can really slow you down, but the added power of the jib makes taking a date along a really fun option. I have the Calvert Boomless Square Top on mine, and love it! I am going to add the Hawaiian Righting System so my crew will have a "sissy line" and make righting easier, and I am going in for the Wave Mast Float. I think the dangers of turtling, or having crew stuck under the sail during a capsize more than make up for any flack my friends give me.The one drawback to the Kit and sails was very limited instructions, and that Calvert and Murrays both forgot parts on mine. Calvert forgot the jib halyard cleat, and Murrays forgot the jib blocks. Also I had expected the Square Top to come with a window, and had to send it back at considerable expence. Be sure to order it with the window from the begining! They were both quick to rectify the minor problems, and I find them both great companies to do business with. The one thing I haven't figured out is mast rotation control without the boom. I got the Murrays kit for that too, but it doesn't provide any way to keep the mast from over-rotating.