As per my understanding the tool should always consider the maximum delay path because it does not know the status of the signal at any point of time. So in case 1->0 delay is grater than 0->1 delay, it should always choose 1->0 delay. The timing path that you see reported by primetime always considers the worst case delays.
It also depends whether you are doing setup analysis or hold analysis.
Skew should not matter in this decision. If skew is present, then the arrival time at the capture flop will change. It will not be one period. It will be less or more. So skew is considered here.