No one (even in fiction) can have a "vision of the future". By that I mean that these characters could only see likely outcomes based on events outside of their influence. Accurate visions of the past? Sure. But if someone sees something coming that they can change, it's not a vision of the future.
The parachutist was coming, and Desmond saw
one possible way that he could find her.
Also, it's not a Catch-22 per se. The episode has the title because the featured book has the title. She probably was reading the book because it pertains to pilots and not because it would have some significance to her mission and I don't think it was placed in there by TPTB as an allusion to Desmond's dilemma.
Also, people are misunderstanding the meaning of a "Catch 22". It's not so much a damned-if-you-do-damned-if-you-don't situation. It's more of a circular logic predicament.
From the book:
There was only one catch and that was Catch-22, which specified that a concern for one's safety in the face of dangers that were real and immediate was the process of a rational mind. Orr was crazy and could be grounded. All he had to do was ask; and as soon as he did, he would no longer be crazy and would have to fly more missions. Orr would be crazy to fly more missions and sane if he didn't, but if he was sane he had to fly them. If he flew them he was crazy and didn't have to; but if he didn't want to he was sane and had to.
Not Catch-22:
- Charlie has to die for the party to get "rescued"
potential made-up Catch-22:
- For an Other to leave The Island he must have his mind right and completed his training. Having his mind right means knowing that The Island is where he belongs and he should never leave. If he asks to leave, his training must not be complete so he's sent to Room 23 for reprogramming.