I usually take my does outside of the rut, so no real worry about a trailing buck. That said this year I have a wt doe tag unfilled. Last weekend whileI could have filled it I didn't as you never know when a single mature doe enters your field of view close to the rut what might be lurking unseen. Though here filling a doe tag isn't really a tough task and with over 3 weeks left to hunt I feel no pressure in doing so.

As far as your first or what to do, I'd be letting your gut tell you when to shoulder and click off the safety. No right or wrong here.

Good Luck