The hull will roll if it is rough out, but any boat will do this. The pre 2004 models were a degree steeper throughout the hull and were said to be more tender, but one degree change throughout will not make a huge change honestly. I've fished on both boats and own a 2004 which is the pre redesign and there is very little if any difference in ride/fuel economy. To have a boat roll less when trolling you would want a narrower boat, but that will take away fishing room and space which is nice when trolling. In 4ft or less the boat is fine, in over 4fters you may feel it rolls a little but it is not any more then other boats, but at the helm it will feel like it rolls more due to the helm bench seats being located more outboard then comparable boats. Also, the boat seems more tender because of the helm as well, when people onboard move around you may need to adjust the tabs from time to time to counter that since their position changce can be extreme. This is a side effect of having a large open helm, but the comfort outweighs that in my book anyday. The 265 is a big 26' boat and rides well for it's size. I've taken my 265 110nm offshore(1 way) in 3-4's with 6's mixed in, and I've ran it 120nm(1 way) in flat calm seas, the boat is very capable. The only real way to tell if the boat is too tender for you is to sea trial one, that may be hard if the boat is not located locally, but with a purchase that big you should be sea trialing the boat anyways. You need to determine what is most important to you, the layout, the open cockpit and space, how much it will roll, or having a narrower cramped boat with a smaller layout with maybe a hair less roll. The 265 will cut a 3-4ft chop running at 28mph without a problem, a smaller boat, even other Grady's may not fair as well, usually a narrower boat will not run as well in a chop, plus a sharper v will slice the chop rather then ride over it and pound down. I believe your waves in the great lakes is much tighter knit and is more of a chop then what most experience so it will perform differently, but a deeper v may give you a better ride to and from the fishing grounds.