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Pictures can be deceiving, but here goes....
Both look as if they've had some leakage/moisture problems judging by the colour and staining of the wood here and there, and in the case of the S2 on the 'carpet' hull liner in the forepeak... the aftermarket hull ports on the S2 require careful inspection too, for evidence of water tightness or lack of.
Most S2s are designed by the G&S team who have a good rep for performance boats.. but I'm not sure all of them were. This one looks like a G&S design.
The Islander is, of course, a Perry design so that's in its favour for sure as a family cruiser. In the pics, though, it looks very dark inside....
I'd get rid of the carpet in both boats.. bad idea all around.. but of course I don't know what's underneath. But a clean f/g liner is a better deal than soggy smelly carpet.
Layouts look similar, cockpits look similar so I guess it would come down to survey and which one "feels" best.....
1984 Fast/Nicholson 345 "FastForward"
".. there is much you could do at sea with common sense.. and very little you could do without it.."
Capt G E Ericson (from "The Cruel Sea" by Nicholas Monsarrat)