OK So I have taken it to a boat repair shop and they are charging me $350 to fix it. My concern is they are going to put a port hole in the deck above the roller damaged area. I will also be adding two more portholes to the hole to repair the wing inlet tubes. Will 3 port hulls in one hull still be structurally sound?
You shouldn't need three ports - and it's not class legal (2 max per hull). You should be able to reach the roller damaged area and the wing tube from the port directly behind the front crossbar. DO NOT allow them to put a port in forward of the crossbar.
Does your boat repair place know what the inside of a Hobie 17 looks like? There are structures inside the hull that support the wing tube and the centerboard. If they cut a port in the wrong place, they (and you) would be very disappointed. The proper way to fix this problem is shown in the "This Old Hobie" article in the Mar/Apr '08 HOTLINE: http://www.hobiecat.com/hobieclass/eHCA ... 4_2008.pdf
You go in through the bottom, not the top. It's a major repair.