Ok, I have a clearer picture of the problem now, and inspired by @walkytalky suggestion, here is a more ellaborate answer.
You mentioned that p1 and p2 travel along straight line segments. I don't know if these segments are aligned in a way such that both p1 and p2 always start new segments at the same time. However, you can always cut a line segment into two line segments (with the same slope) so that both p1 and p2 always start new line segments at the same time.
Assume p1 travels along line A-B, and p2 travels (at the same time) along C-D as a parameter t goes from 0 to 1. (That is, at time t=0.5, p1 is in the middle of A-B and p2 in the middle of C-D.)
By letting Ax and Ay denote the x and y coordinate of point A (and similarly for B, C and D) we can express p1 and p2 as functions of t in the following way:
p1(t) = (Ax + t*(Bx - Ax), Ay + t(By - Ay))
p2(t) = (Cx + t*(Dx - Cx), Cy + t(Dy - Cy))
(For instance, when t=0, Ax + t*(Bx - Ax) evaluates to Ax, and when t=1 it evaluates to Bx.)
To find each "a-vertex-is-passing-by-between-p1-and-p2"-time we do the following:
For each obstacle vertex v=(Vx, Vy) we need to find a t so that p1(t), p2(t) and v are in line with each other.
This can be done by solving the following equations (two equations, and two unknown, t and k):
Vx=p1(t).x + k*(p2(t).x - p1(t).x)
Vy=p1(t).y + k*(p2(t).y - p1(t).y)`
If k lies between 0 and 1, the polygon vertex v is actually between the (extended) A-B line and the (extended) C-D line. If t is also between 0 and 1, the vertex v is actually passed by the p1-p2 line during the time the points travel along these segments (since when t is, say, 1.3, the points will already be on new segments).
Once all "a-vertex-is-passing-by-between-p1-and-p2"-times has been computed, it's a simple task to figure out the rest. (That is, figuring out if it is a "becoming-in-sight", "becoming-out-of-sight" or "neither" type of passing):
For all pairs t0 and t1 of consecutive vertex-passing times, you check if the line p1((t1-t0)/2)-p2((t1-t0)/2) is free of intersections with a polygon edge. If it is free of intersections, the points will be in line of sight the entire period (t0-t1), otherwise they will be out of sight the entire period (since no other vertices are passed during this time period).