One of the great modern rollers is Dubside, he has clearly shown us that you can roll just about anything somehow. But Dubside will be the first to admit some kayaks will be easier to do certain types of rolls than others, making the probability of success higher and the learning process easier. There are also many things you can do to make you kayak more suitable to roll.
On my 40th birthday I was fortunate enough to be given a great modern rolling kayak, the Tahe Marine Greenland, which is a fiberglass replica of a 1900 century western Greenland design Qajaq. My other main kayak is an NDK Explorer, which in my opinion is one of the best all-round kayaks which does everything well. The Tahe has a hard chine hull shape with a fair amount of V to its bottom, this is especially helpful for forward finishing rolls where a smoothly rotating hull is desirable. There are flatter hull designs that make the more advanced layback rolls like the elbow and straight jacket roll easier. The flatter hulls are like planks of wood, they like to end up flat on the water and tend to flop down at the end of the roll helping it to finish. The ideal hull shape for a forward finishing roll is like a log which freely rotates. Clearly a compromise is needed if you are to have a versatile kayak, and I have found the Tahe makes a nice compromise.
When I picked up my kayak I used it without any modifications, but as my skills evolved so too did the Tahe.
First I removed the back strap as this prevented me from laying back and also got in the way during re-entry and roll maneuvers. I then fitted a fixed foam back rest to reduce the bruising I experienced across my lower back where it arched over the cockpit coaming. My next modification involved constructing a foam masik (the low deck beam in skin on frame kayaks that goes across the thighs.) When learning the reverse sweep roll I found that numerous times I would become disconnected from my kayak when stretched back and upside down. My knee and thigh would lose contact with the foredeck and I would be unable to perform the knee raise/pressure necessary to roll up. I tried the roll in a friends traditional skin on frame kayak and was the successful. The kayak had a very low deck beam just in front of the cockpit, called a masik, this beam was constantly in contact with my thighs and this tight fit really hepls maintain good contact and the appropriate body position throughout the rolls. I made my masik from high density closed cell foam and this I fit between the deck and my thighs. Yesterday I removed the masik and found I was now able to complete all the rolls without it, but I think it was an excellent training aid as it removes a substantial variable and allows you to focus on learning the muscle memory for each roll without worrying about where the kayak is in relation to your legs.
My next modification was to remove the foot pegs that the Tahe comes with and replace them by filling the front of the cockpit with high density foam, this allows me to easily find the correct foot placement at all times during the rolls and also is warm and comfortable – I think this is more a personal preference than an aid to rolling. It does have an advantage after a wet exit as it reduces the volume of the cockpit which then in turn reduces the volume of water that can flood the cockpit.
My final modification was to remove the plastic seat from the kayak and replace it with a thin sheet of foam. This lowered me about three quarters of an inch which helps get my body mass where it needs to be, nice and low in the kayak.
There is some debate amongst the rolling community about hip padding; how much room do you want between your hips and the kayak. I currently do not pad out my hips, I prefer instead to be have the freedom to move and rotate and arch within the cockpit without my hips being constrained, again I think this will depend upon the type of rolling you want to perform and probably comes down to personal preference. Dubside comments on how in some wider kayaks it can be an advantage to offset your body mass by sliding to one side or the other to help finish rolls.
Oh and I forgot – add some deck beads to your kayak to help stow your paddles. Another deck bead post here.
So clearly there is lot that can be done to make a kayak easier to roll, getting your kayak set up right for your body size and shape will certainly help you learn to roll and can make a lot of difference to the comfort. I recommend you invest some time fitting out your kayak to find every advantage you can get during your early learning experiences.