Yes, of course it's tougher as at least one of te players has to survive the first 15 picks (not 31).
However, the likelihood that a player is picked randomly is 1/48, i.e. the probability that he is not picked is 47/48. If he is left the second round the probability is 46/47 and so on to the 15th round where his probability of "survival" is 33/34 = 97%.
As he has to survive all these picks the total probability becomes 69% that he is left. The probability that
both the first picks are left is 47%. Finally the probabilty that at least one of the first or second pick is left is 91%!
That is, in a league like yours where almost all teams are bots you are very likely to get either you first or second pick. Ragans league is much more active, so of ocourse this decreases his chances. However, I would believe that quite a few of the active teams do not really care that much about the draft (just as a lot of teams dont seem to give a damn about their arena). Thus I would still think that he has a quite good chance to get one of his first two picks.
I hope a did my calculaions right now. It's a long time since I calculated probabilities. Probably about a decade or so.
