RE: how many times
No. I never drew back on any deer until the first one I took came into range. Before that, I was screwing up basic hunting skills and just not seeing deer. ie: spooking them on the way in, poor scent control, too much movement, etc. After my first two seasons, I ironed out most of these problems. My first deer walked in when I was out of the stand heading home. I was on the ground, out in the open but with decent background. The deer walked broadside right in front of me at a near perfect angle. Unfortunately, I hit it up high on the spine. This was right behind my house too so dragging it home was easy.
The next year, I shot at a spike on the last day of the bow season. The shot was low and went right under the boiler room. Finally found the arrow and was thankful for a clean miss.
-Mike