What does "skepticism wins" mean?
If what is right--that you can't be sure you're not dreaming? Of course that's right; how would you ever tell? Any method of distinguishing you came up with can't possibly be relied upon, because if you are dreaming, then that method only works in your dreamworld. In other words, it can distinguish between meta-dreams and dreams, but not between dreams and reality. (And there's no real reason to think it can even do the former, because hey, it's a dreamworld after all, and no rules apply.)
You search because you're looking? What does that mean?
Here's a question. I assume you are familiar with the probability-theoretic notion of maximum entropy. By "radical skepticism" do you mean the thesis that the only possible rational belief-state is maximum entropy?
It means we cannot be justified in knowing anything, and are isolated from any objective reality. The basic rules of probability from which we assume the reliability of memory, senses etc are taken on religious style faith.
I've been trying to find a way around this, but you are probably right.
I mean I am checking and and again just in case because I don't like the idea that scepticism is right.
I'm not familiar with that notion.
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.