You need be to do more research into both the boats and the conditions on the coast of Maine.
Do you have a kayak already? How much experience do you have?
My first thought was " I hope he doesn’t drown."
Longer boats have more hull speed. That means that you will get a lot more distance with less work.
The skeg might just have sand clogging it. That has always been their problem down in Fla., though I don’t know how Valley does their skeg box or if it is just an aftermarket one.
My thought is to keep looking, there are lots of used boats out there, why limit yourself? Ask those friens what kind of boat they would love.
I’ve owned the LiquidLogic Sylva so I have some input. I purchased it used for use exclusively on a lake; it was my first smaller kayak and fit me much better than the WS Tsunami 145 that we’d bought, and I really liked it. However I’d say it’s more a transitional boat between a recreational and a sea kayak, and it does not have continuous static deck lines so is not suitable for kayaking in the ocean. Also the cockpit is too large for this purpose. It was great for kayaking on a calm lake. Don’t know anything about the Skerray but would not suggest the Sylva for the ocean.
I agree with Celia to keep looking. Lots of used boats in Maine.
Don’t know your size or location, but there’s an older Romany pretty near Portland for sale for $900. If you liked it you could offer less.
Most people in a group that I paddle with on the Maine coast use 16-17 footers, but there are a couple of 14s that seem to do just fine. But you can compromise a little on safety in a bigger group because help can be at hand. If the Skerray is the gray one in Raymond on Craig’s List, I noticed that it doesn’t have thigh braces on the cockpit rim. You can still brace directly against the rim, but it can be less comfortable. It’s also a sort of darkish gray plastic that won’t be very visible. That’s something to consider especially if you paddle alone. And the Valley hatch covers have a bit of a faded black appearance. Check those hatch covers carefully as they deteriorate with age and perhaps factor in the cost of replacing them. To me, the price may be a toward the high end (depending on condition) but early summer may not be the time to get the best deals. If you’re not in a big hurry, more choices should come up.