For Riddler Classic, consider that you have a tree of N vertices, and that you know the expected value E[N,p] of the number of connected components for N islands that collapse with probability p.
Now, make a tree of N+1 vertices by adding a leaf node. What's the expected value now? If the new leaf node collapses, then the expected number of components is the same as the N vertex tree.
If it doesn't collapse, then there are two possibilities. If the node you attached the leaf to survives, then the number of components stays the same. If it doesn't, then the number rises by 1. Since the node collapses with probability p, the expected value will rise by p when the leaf survives. Therefore:
E[N+1,p] = p*E[N,p] + (1-p)*(E[N,p]+p)
Since it's possible to construct any tree by starting with a single vertex and keep adding leaf nodes, the previous equation says the expected value depends only on the number of vertices, not on the tree's topology.
In particular, we can calculate it for the star shaped tree, where we have N-1 vertices connected to a central one. Now, if the center doesn't collapse, we always have 1 component. If it does, then we have N-1 independent expected values of 1-p. Calculating, we have
E[N,p] = (1-p+Np)(1-p)
And you can verify it satisfies the other equation as a sanity check. If N=1, it's maximized for p=0. For other N, expand and derive with respect to p, equate to 0 and find
p = N-2/(2N-2) ,
which is always a well defined probability, since N >= 2 implies p >= 0 and 2N > N implies p < 1.
EDIT: It seems I missed an easier way to calculate E[N,p]. The first formula is just
E[N+1,p] = E[N,p] + p(1-p)
Using the fact that E[1,p]=1-p, the expression for E[N,p] follows immediately. Curiously, since you guys are mentioning OEIS, it seems this problem deduces a stronger result than what's known there. By plugging p=1/2 and multiplying by 2^N , we get the total sum of connected components formed by all vertex subsets of a tree of N vertices. That gives
A(n) = (n+1)*2^(n-2)
The first numbers are
1, 3, 8, 20, 48
This is
https://oeis.org/A001792
It's written there: a(n) is the number of runs of consecutive 1's in all binary sequences of length (n+1). - Geoffrey Critzer, Jul 02 2009
It turns out this is a direct corollary of the previous result. Binary sequences represent whether a vertex is included in a subset or not (0 if it's out, 1 if it's in). A run of consecutive 1's is simply a connected component of a tree with the topology of a line: 1-2-3-...-n
So, someone should probably publish a paper so that we can strengthen the result at OEIS (or perhaps the guys at Riddler have already done it, I know it's common practice to make exercises based on elementary results that you derived on research papers :P)