I'll also take a stab at (2)
Consider square ABCD below:

This square is divided into 8 equal areas. It is clear that P cannot fall anywhere into rectangle ABFE because, although triangle APB and and triangle DPC would have equal bases, DPC would always have a greater height, and thus, a greater area.
It's also clear that P cannot fall into area IFC......To see this, note that if P fell on AC, its distance from AD and AB would be exactly the same. But, if P falls in area IFC, its distance from AD would always be greater than its distance from AB. Thus, triangles APB and APD formed by having P fall into this region would have equal bases, but APD would always have a greater height than triangle APB.
For the same reason, P cannot fall into area EID, because all triangles BPC would have greater heights than triangles APB.
So, P can only fall into region CID. Here triangles APB, BPC, CPD and DPA will all have the same bases, but APB will have a height greater than the other three.
And since CID is 25% of the area of the square, the probabilty that APB is greater than the other three mentioned triangles is ≈ 25%
