Sorry to appear naive, but I am not really sure what you want or what you expect. Are you asking for a complete re-design/re-drawn of your pictures? If so, what are you expecting? A single color (ie. black) that is easy to weed?
I am new to the vinyl stuff, but not new to graphics. A little trick I learned in photoshop, which I can take nearly any graphic and convert it to a vectorized, one color item that is not impossible to weed. Example, I took your photo of the Indian with the tablet, concerted it to black & white. Next, a trick that I learned along the way when doing this is that it is important to blur the image just a little... it removes a lot of the tiny details (which make weeding impossible). So I use the box blur, but only a small amount... then lastly I hit it with the photocopy plugin... then use the eraser to clean up the outer areas and such. Then vectorize it in VinylMaster Pro. See attachment. Is this what you are trying to do?
new.eps