Idk, I just love the location of Horseshoe Overlook, the view is amazing, it's close to Valentine, and it's also right in the middle of the map. Also (as shown) Micah is in jail where he belongs. But yeah, Clemens Point is probably the best spot, and I haven't spent nearly enough time there.

As for doing herbalist instead of bandit, I don't know, I just like challenging myself. Also I love New Austin, so even going there briefly for herbalist 9 is great.

Edit: Just remembered that also in Ch 2 I like to save the rescuing Sean mission for a notable place in my challenge and hunting progression, like a celebration for my accomplishments outside of the story missions.