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IIRC there are ~12000 5 letter words and he got his partner to go through the ones she knew which was ~2500. Those 2500 were randomised to be the answers but the guesses can be any legit word. So the answer will always be reasonably common
This tallies up with my experience and what I posted a few days ago about 'trying to be too clever'. In my experience the answer is more likely to be a common/simple word than a more obscure word. So skill is more likely than swill and train more likely than argon.
ElGonzo-
But once the 'common' 2500 words have been set, there's equal likelihood of them being the answer. So if both swill and skill are in the answer list, either will have the same chance of being right. eg Older and Elder.
I suppose it's down to how wide one's knowledge of 5 letter words is compared with the setters'. But you're probably right in general - I guessed Elver in the Elder one so guilty of exactly your point!
villa-ru
There was a NY Times article about it. IIRC there are ~12000 5 letter words and he got his partner to go through the ones she knew which was ~2500. Those 2500 were randomised to be the answers but the guesses can be any legit word. So the answer will always be reasonably common and there are loads of obscure words that never will be the final answer but are obviously still useful as guesses. But there is no reason skill should be more likely than swill or argon less likely than train. I think.