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.
Just to reiterate what someone said above: ocean cockpit = hard no.
With your knee it will never work. Heck, OCs don’t work for most people, even the young and lithe. I once trained a young guide who had got a great deal on a Nordkapp HM with an OC. His frustration with the cockpit was evident and I knew it wouldn’t be long before he passed the boat along to someone else.
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For those that hear the term ocean cockpit and don’t know what it means, here is an article from a while back that describes it versus keyhole (what is standard nowadays)
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When I answered in post number 6 I didn’t get from your OP that you were also looking at moving from WW rivers to the sea.
For me that would be like me thinking about going up to Lake Erie with my canoe and that would be 99% out of the question unless I planned the weather carefully and made my trips quite short and close to shore.
I assumed the knees were the problems and you wanted to continue where I was familiar with seeing you paddle from your photo logs.
Taking on the ocean is a whole different skill set and something I know little about.
Sorry for the confusion earlier in the thread.
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I was a little unclear. My knee is a problem, or it will be eventually. I was able to kneel in my canoe over the weekend for a whitewater run. On Flatwater trips I spend a lot more time sitting now, so why not get a sea kayak. There are of lots of great sea kayak trips around here (rock gardening and touring) I can’t do in my canoe.
A little late for the reply, but here goes… considering your enjoyment of ww, you probably would like a sea kayak that falls more in the play category. I think the stratos is a real good option. Another one might be a Delphin 155. It has lots of room, and is built for play. I’m 6’5", and my sea kayaks are a CD Isle, Prijon Marlin, Jackson Journey, and P&H Hammer. The Isle and the Journey have huge cockpits (they both take a Seals 2.2 skirt).
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Thanks for you input - you have a nice mix of boats.
Obviously early in the process, but I haven’t found a Stratos or a Delphin 155 around here. I’ll keep looking, but I’ll probably end up buying something a little longer to start. I can always upgrade or add to the fleet later. We’ll see. 
Are there any experienced retailers, like “The River Connection” (Marshall) for example, close to where you are - where you can try out a few different kayaks?
Here you go… Valley BOGO (buy one, get one):
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Here is a video of longboat surfing with a Delphin 155 and an Avocet RM. (Also, more than few examples of dangerous “party wave” surfing…):
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Another idea, if you’re willing to part with the money, might be the Romany Excel. It’s light, playful, with a relatively large cockpit (I was not able to fit into the Explorer but I could shoehorn into the Romany S and had room to spare in the Excel). Kayak Waveology in Conn might have some, or the Boston NDK dealer.
Kayaks allow much less freedom of movement while paddling. I find that canoes are much easier on the back, knees, and hips. Find some good canoe seats. Lower them if you want to. I think you are heading in the wrong direction.
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All true, but if I want to paddle in the ocean I can’t do that in a canoe. I’m not giving up my canoes for flatwater paddling. I’ll probably lower the seat in my Wildfire and make that a sitting boat.
Kayak Waveology has a lot of beautiful boats (I think the ones you re referring to), but they are WAY above my budget.
https://kayakwaveology.com/store/
I might consider the Explorer at the bottom of the page for $1,500 if I could fit in it.
That does look like fun.
Someone else suggested that I call them - its the closest dealer for P&H kayaks to RI.
Would I fit in the Advocat - I sent an email to see if they would sell separately.