1. Yes. 2. Your odds are the same as his for that particular hunt, but he has a higher chance of drawing a tag because he is in 4 drawings.

I only put down one hunt for deer, and two for elk. If I don't draw any special permits, I have some pretty good plan B's. If I don't draw these hunts, I don't want to waste my points.

I suggest finding a permit area that you like and just keep drawing for it. It took 4 years to draw this tag.
I have 1 point going into this next drawing, so chances are slim I'll draw, but then again, its 10:1 odds for this hunt, so I do have a chance.

They have switched the doe and cow permits a bit, so that if you draw antlerless only tag, you do not lose your points. "Any deer" or "Any elk" tags will bring your points down to ZERO.

Good Luck!