After a bit of hemming and hawing about my next boat purchase, a SOT surf kayak is looking like the winner over an upgraded touring boat (lots cheaper too!).
I’ve had a bit of experience with rental SOT boats in the surf - OK Frenzy, OK Yak Board, Islander Hula - and found all of them a bit limiting due to lack of thigh straps, and their more general-purpose designs (the Frenzy’s keel didn’t help). I’ve also used a WW boat on one occasion for a surf lesson and had side-surfing and basic bracing techniques down by the end of the day - it was certainly a lot more capable, but my lack of a bombproof roll made the SOT experience a lot more fun. I’m a smaller paddler (5’5" 130#), am looking to use it on various locations on the East Coast, and want one that has considerable growing room in term of skills.
I’ve perused the message boards and the boat reviews, as well as a number of surf kayaking-related articles (most notably http://www.sit-on-topkayaking.com/Articles/SurfSail/SurfKayaks.html), and here are some of the leading contenders so far:
OK Rrrapido
Perception Five-O
Islander Lipstik
Cobra Strike
I’ve also read reviews of the WS Kaos and Cobra Wave Witch that made them look like less-than optimal matches.
As I’ve seen quite a few spectacular winter sale deals on used/demo models of all of these boats, I might even take the risky step of buying before trying (gasp!). Any of these strike you as either a particularly good or bad choice for the usage parameters I’ve specified? And are there others I should consider? And for any of these boats, what accessories are recommended (lifejacket, helmet, short paddle, and thigh straps are assumed)? Thanks to all…
Warning!!!
Be Careful What You’re Getting Into!
I say that because paddle surfing is very addictive. If you get hooked, you might as well accept that your first craft will not be your last. Case in point: I started on a Cobra Strike, moved to a Wilderness Systems Kaos, then to an Infinity wave ski and now I’m learning the performance capabilities of a Mako Aquarius surf kayak. Each step along the way, I thought I would be satisfied with my acquisition…but soon longed for the next step up in performance.
I’ve not tried the others on your list of prospects so I can only address the Cobra Strike and the WS Kaos. But rather than fill a bunch of space here, if you haven’t already, check my reviews of both the Strike and the Kaos on this site. Both have their pluses…and some minuses. Given your size, one challenge will be weight. Most of the plastic boats come in at 35 to 40 lbs…a lot to be hefting around, both in and out of the water.
Saying that, I still think starting off with a roto-mold SOT surfboat is a good beginning. This will allow you to launch your wave-riding career in a durable, stable craft without incurring a major start up cost. Since it might just be a stepping stone, used would probably be the way to go.
As to a roll, I struggled with that confounding maneuver for a long time. In fact I didn’t even start trying until I started riding my wave ski…which by the way can be equipped with thigh straps. Over time I developed a dependable roll and that has allowed me to start surfing a closed deck surf kayak where a roll is essential.
Regarding equipment, starting off I would recommend a PFD and a helmet. Some folks also prefer to have some kind of leash to tether them to their paddle craft. And since you’re on the east coast, you’ll need water-ware that will keep you warm. Count on being in the water as much as on the water…so dress for emersion. There’s an interesting article on an appropriate water-wear on www.sopsa.org in the Journal section under the title Dress of Success. The length of paddles for surfing is trending toward short…173 to 178cm.
Feel free to e-mail me if you have any questions. As a confirmed “addict”, I have developed a deep experience base that might help you with your decision process.
You’re too late, JLK… 
…I’ve already caught the bug. Every time I’ve been near the ocean since my first surf lesson with enough spare time and when the weather isn’t too much for my immersion gear, I’ve been goofing off with some rental boat in the surf. So it’s time to get a little more serious by getting my own boat and making sure that more of my vacation time is spent in close proximity to some tasty waves. 
No SOT Comments But
You may want to check out the Virginia Beach Surf Kayakers, if they're close to you. Seems like a real active group of surf kayakers. It's an opportunity to surf and learn from others, try out boats perhaps, and to have a little more safety with partners out in the break.
I love their webpage. Lot to explore in the site:
http://members.cox.net/vbsk/
sing
PS. If available, pick the SOT with the fin option.
I Like The Strike
I am not surfing much these days, and still surfing the Frenzy when I get chance, but I have used the Kaos and the Strike for lessons/guided trips in bigger waves.
I like the Strike better because it is more forgiving when you catch a big one deep. You can pay dearly for a wipeout on the NORCAL Coast. The water is cold, the waves are big, and the coast is rocky.
At your size, the Rapido might also be a really good boat. I am too heavy for one. They are no longer in production. You would have to find one used.
I surfed Virgina Beach with a longboard when I was young. There is pretty decent surf there sometimes, but 4-6' is a pretty big day. You might think about going straight to a wide waveski like the Island EZ and equiping it with thigh straps and a backband. I have seen it done and it seems to work. They can be a litle fragile, but should be OK on sandy beaches.
As JLK noted, especially for a beginner, surf kayaking is a swimming sport.