I've raised arguments for philosophical scepticism before, which have mostly been argued against in a Popper-esque manner of arguing that even if we don't know anything with certainty, we can have legitimate knowledge on probabilities.
The problem with this, however, is how you answer a sceptic about the notion of probability having a correlation with reality. Probability depends upon axioms of probability- how are said axioms to be justified? It can't be by definition, or it has no correlation to reality.
In that case, I don't know how to proceed until you formulate your skepticism more precisely. What exactly is it that is not justified, if "skepticism wins"?
Nothing is justified if skepticism wins. Unless we have irrational faith in at least one starting assumption (and it is irrational since we have no basis for making the assumption), it is impossible to determine anything except our lack of knowledge.
So on thought, yes. There is never any valid rational reason to discriminate between possibilities because nothing can demonstrate the Evil Demon Argument false.