Plothole?

I would like to start this post by saying it has been a few years since my last viewing of this movie, but I am fairly certain that my observations are still correct.

So, Jennings sees himself die in the future. He is supposed to die in the room where he is strapped to the chair, relatively early on in the movie. He sends himself the special sunglasses and cigarettes to save his life. So far, so good. The problem I see is everything after that. If Jennings dies there in the vision of the future, how can he see further into his future to know what he would need to survive. He would have died in the room with the chair, so he would never have gotten to the point where he needed anything else than the cigarettes and glasses to MAYBE make an escape.

So, the obvious solution is, Jennings DID send himself the glasses and cigarettes, so he DID make it our if the chair room in his next viewing of the future, and therefore could see the other items he would need. Right, but in that case, the items would have been in multiple envelopes. Every time Jennings saw a death for himself (or a friend), he would send an envelope to himself to help out,

I say all of this based on my somewhat hazy memory of the movie. I remember this being my only thought during a good portion of the movie, and I think it was a big part of me not enjoying the movie all that much (kind of stupid of myself, I know). An I right? Was this explained somewhere in the movie? I know it's just a small flaw if it's a flaw at all, but it is one that bugged me at the time.



Wash dies. Damnit!