On a Brooks: at the start level the nose, not the whole saddle
Generally, the placement of the rails is such that you will need to push it back. Brooks are somewhat well known for this.
Yes. The leather is hard to start with. Sturdy leather is why Brooks can last more than 30 years, like MimiTabby's B66.
Proofhide is your friend. Apply liberally.
Break it in like a sturdy pair of leather hiking boots.
Last but not least: figure out where it's pushing on your soft bits, and push back! (with your hand) Lean on that spot during commercials while you're watching TV. (assuming your bike lives in the house, like mine.) You custom form the leather to your anatomy over time. For anatomical bits that can't push back, you gotta give it a try by pushing with your hand. Get that spot of leather softer and see what happens.
And remember, Wallingford gives you 6 months to make a decision.
"If Americans want to live the American Dream, they should go to Denmark." - Richard Wilkinson