No, once you pick the cucumber or even if it aborts another one will not come from the same spot.
I have never topped off the growing top of the vines but I know they do make side shoots. I would leave them even if they reach the top of the trellis. As to the male flowers, they will pollinate any of your cukes they don't need to be the same variety. If they are not setting maybe you don't have any bees working?
