First, is it better to write the whole screenplay first and then just jumble it up and add transitions in between the "jump" points, or to write the jump points into the screenplay as you are writing?
My opinion {and it's worth every pfennig you paid for it} is to have the whole thing
plotted out first, at least in outline form, maybe on cards (
a la Blake Snyder), then determine which points in the story are the best, most logical ones for your viewpoint shifts.
it is just showing different parts of her life at different times that I want to accomplish, jumping the story not the character actually time jumping.
This is a tricky thing, or I perceive it
can be, so my recommendation is as above... get the sequential events set first before you dump it in the Cuisinart.
The second question is, how much jumping of the story would be too much to where it becomes almost obnoxious or confusing?
This question, I'm going to give you as good an answer as I can.
It might not be enough; let's see... I say if you can follow it, and someone whom you give it to can follow it, then it's the right amount. If
you get confused, and you
wrote it, how can anyone else not get confused as well?
In summary, just write it so it makes sense to
you, and try not to be deliberately confusing. If people who might make up the target audience demographic for your movie follow it, then you did it right.
Write On!
Cheers!
Al B.