If he' s looking for his first deer with a bow, why would he let does pass by and wait for a buck? A first deer is a first deer, no matter what. Once you get a few of them out of the way and you' re confident in your ability to harvest an animal with a bow, then he can start trophy hunting.

If I was you, I would sit the rifle stand that has good sign near it. Sounds to me like your chances of seeing and harvesting a deer from that stand are the best. If things don' t work out and you dont get one - it won' t be disturbed much, if at all, by your presence there and still be a good spot for the gun season.