This is for sony vegas...
multiple screens- Select the pan crop thing on your video, scale it down, and then set it where you want it. Create multiple video layers and do this for each video you want. You may also want to use the picture in picture cookie cutter for a border of some sort.
Dark circle outline- I am not sure exactly what you want with that, but heres where I'm guessing you want.
One a or b work depending on what exactly you want it to look like. the second step is the same for both.
1a-Take your video, get the oval cookie cutter, and make it as big as you want. I would also feather it a bit, but thats just me.
1b-Go to the pan crop screen, get the pen tool, draw your border, feathering and adding curves to your liking.
2- Add black below that.
Pretty simple. What I think can be pretty cool with this is have the same video below the masked video with a dark brightness/contrast setting, instead of the black. just an idea.
Sorry if this didnt help.