Yes, so you have a sense of the boat from that RM version. You got to figure that the lighter carbon/kevlar will have a little more zing in getting to speed because it’s stiffer and lighter.
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Another to try is a Stellar S16S. I have the S14S and it is a tight fit.
I would think a SOT would be a good choice. I have a bad knee but do well in my sit in sea kayaks. However, in a sit on top you can even hang your legs over the sides when stopped.
Edging and a bow static draw might make your turning while moving easier.
Not sure who is teaching now at the Kayak Centre but I used to work there - if it’s Ken tell him I said hi! (Brooke - he’ll know me). They’ll put you in an appropriately sized boat, and you might be able to try a couple if there’s time.
The Valley Skerray is an ocean cockpit boat - definitely something to stay away from if you’ve got cranky knees.
Agreed that the Delphin, Stratos/Alchemy, P&H Virgo or Valley Gemini are all great plastic all around sea kayaks.
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Yes, used is the best bang for your buck.
Do not limit yourself to rotomoulded, definitely consider composite kayaks as well, they are much tougher than people give them credit. This very topic about how rugged a composite kayak is came up in the recent topic about gel coat repair.
Hey Eck, it is all good- meaning canoes, c1s, kayaks (sit ins and sit on tops), rafts, ducks. There are a lot of things I still miss about canoeing and c1ing. I don’t miss the pain. It is great to still get out even if it means I do it a different way now. Good luck finding the right ride.
I actually find narrower boats put less stress on my joints (better boat/body connection) but they are harder to get out of. I got no pride and ain’t afraid to ask for help (having someone hold the boat, or pulling it up partway on shore) or I just get wet when exiting the boat… the trick is not to submerge the cockpit because then the boat is harder to drain. As far as me staying dry, that’s not a priority. Paddling is good, regardless of the type of craft. Just find out what works for you.
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You guys must not do as much rock gardening as we do out west. On our club trips, no one bats an eye at a 14’ foot boat, like a Dagger Alchemy or Stratos, on all except the longest paddles. I don’t currently own a boat longer than 14.5’, so guess I wouldn’t be allowed on your club paddles.
On sit ins and being in one position for a long time, and you hearing about white water people complaining about this. All sit ins you are wearing, much more so than a canoe or sit on top. But the fit is much tighter in white water boats than touring boats. We generally have some room to move our legs around in touring boats, where white water boats usually don’t.
If you do end up with a sit on top, you can often get thigh straps which will hep you get more performance (edging and the like) out of the boat.
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The sea kayak characteristics of your local club is pretty standard. 14 ft kayaks (i.e. Stratos, Alchemy, and a few others) that have all the other characteristics are usually not a problem.
Regarding cockpit size and kayak fit, make sure you can easily get in & out of the kayak - this can be tested on dry land. As another said, no ocean cockpits for those with limited leg mobility. As you are used to a canoe, a sit in sea kayak may seem very enclosed to begin with.
WW paddlers seem to wear their kayaks. Sea kayakers (at least me) like to be able to engage all 5 contact points, however not to the point of wearing a tight fitting kayak. What this means is that some of us like being able to adjust our legs a little on long paddles. Moving some does not mean we slide around inside the kayak. I owned & liked the CD Sirocco and rolled it, however even though I am 6’1" and (was) 205, there seemed to be enough room to play a game of handball in the cockpit - you probably do not want a kayak that loose.
Should you decide to learn to roll, you will gravitate to a sea kayak which allows you to engage the points of contact more easily. This can be done by buying a tight fitting kayak or installing pads for greater contact.
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Like anything - it depends on the paddler. Experienced paddler like you shows with a 14’ boat and no one blinks an eye, newbie like me shows up and that would be another thing. More than anything, I think the requirement keeps inexperienced flatwater paddlers from showing up on sea kayak trips that they don’t belong on. The guy who owns the sit on top that I borrowed regularly paddles a 14" Tsunami Ranger sit-on-top. Rules are made to be broken - by the right paddler.
I feel pretty confident saying if you are ever in RI you can paddle your 14’ boat with RICKA. 
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There is a P&H Aries 150 for sale near me - $2,000. Not plastic, but the price seems right for a composite boat, and I can do a demo. Assume it is similar to the Aries 155 - just half a foot shorter.
You won’t fit the Aries 150. It’s intended for small to medium size paddlers.
Half the RICKA contingent I was out with recently for the rock and surf play trip were in Aries 155s.
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Thanks - I’ll keep looking.
The Aries is a better boat in every way than the Delphin except for two: price and durability. The flat bottom of the Aries is slightly prone to cracking under real duress, such as dropping off the back of a big wave when busting out through surf. A friend had this happen to him and he adjusted for it by landing at a slight angle rather than flat.
That said, I would happily exchange my Delphin 155 for an Aries as the paddling experience is just slightly better in every way.
Oh and this: carrying a Delphin is unpleasant. Between the weight of the plastic, the aftward positioning of the cockpit, and the positioning of the thigh braces, it is no fun lugging this boat any distance.
That’s why I traded my Delphin 150 (as much as I liked how it surfs) for a Sterling Progression… What a difference on those long (100 yard plus) carries to the beach break. I think I probably added a couple more years of long boat surfing with this switch. 
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I would definitely avoid the Silhouette (And my better half is the one selling it - don’t tell her I said that). You basically sit in it with your legs out almost straight because the deck is very low. Fantastic boat, but at 5’7" and 180, I push the limit of comfort sitting in it. Shame, because if I could stay comfy in it for say a 15 mile paddle, we’d keep it, and I’d paddle it. Same reason I sold my Betsie Bay a few years ago - legs out too straight aren’t doable for more that 5 miles or so anymore.
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The current Delphin’s with the Corelite X construction are in the same weight range (25 kg) as most of the Aries constructions. I haven’t gone 100 yards with mine (2020 model) but I’ll often carry 75 yards from the landing to where I park. I do agree that the OP probably wouldn’t like a 150. I will say that I’m 5’ 8" , 155 and the 150 is roomy.
Going back to your original list…
Without seeing the actual ads or boats listed, there are some limits to what I can advise, but–I own both a Pintail and a Skerray and have owned and frequently paddled both for many years. I love both boats, and use them for different purposes.
Both boats have variants with ocean cockpits (short fore-aft dimension). Most Pintails have these ocean cockpits, but only a minority of the Skerrays do. If you are older and having knee problems, I would advise strongly against buying a boat with an ocean cockpit–even though, personally, I like these small cockpits a lot. You are likely to find entry and exit difficult, possibly even painful.
The Pintail is a poor choice for your first sea kayak. While highly maneuverable and a great rough water boat, it is not directionally stable (it’s completely dependent on good–i.e., very good–paddling technique to keep it going in a straight line), and as noted by a poster above, it is small and tight fitting.
The Skerray is a bigger volume boat, comes in both plastic and fiberglass, and most have keyhole cockpits. If it fits you, then a plastic keyhole version could be a good choice for you. I use mine (plastic) mostly for instructing, swim support, and rock-hopping. Its toughness and extra buoyancy (larger volume) fit it well for those roles. It’s faster than the Pintail in flat to mild conditions, and still quite maneuverable. It has good primary stability, excellent secondary stability and rolls easily. I think it is a very good boat in which to learn stroke refinement, edging, bracing, and rolling.
Good luck!
The Skerry is plastic with an ocean cockpit. I sent an email to the owner, but haven’t heard back. Maybe it is sold.