I understand what Susskind is thinking
Just to be clear: you realize he is arguing that fine-tuning isn't fine-tuning given the multiverse cosmology he refers to (albeit I think with his own special name)?
but you are not taking into consideration what I said above.
I did. Perhaps I wasn't clear about what happens when you talk about selecting one out of an infinite number of outcomes.
You could keep picking from that infinite deck for all eternity and never pick the ace of spades.
1) It isn't really accurate (and I can't see it being helpful) to think of this as picking possible outcomes (I used that analogy just to explain why Susskind favors a multiverse cosmology). As long as we're talking physics, often enough a quantum system has an infinite number of values for some observable, but we will only end up with one value (this is unbelievably over-simplified, but I don't wish to get bogged down in the technicalities of QM). We don't keep trying for a value, we just get one.
2) Given any infinite set of possibilities s.t. the set is either infinitely dense (such as the rationals), uncountably infinite (such as the reals), or consisting only of equally probable outcomes (any infinite set), the probability of any outcome is 0.
Probability distribution functions are frequently continuous. Continuity means that the set of outcomes consists of all reals in the interval [0,1]. That number of outcomes is larger than the set of rational numbers. It is uncountably infinite. The probability of any outcome is 0 because it is infinitesimally small.
The rational numbers are similar. They are countably infinite, but are infinitely dense (there exist infinitely many "points" between any two "points"). Thus, for any particular value, the probability is 0 because the value is infinitesimally small (we've removed the limits by removing the reals).
If the probabilities are countably infinite but not infinitely dense, then we could have non-zero probabilities for outcomes. However, if all outcomes are equally likely, we're dividing 1 by infinity, and we still get 0.
Yet in all of these cases, in actuality we still get outcomes.