In my opinion, the Internet and other societal factors have made people overly precious about pipe smoking methods and techniques.
The following is my take on breaking in a pipe.
1) Select the tobacco you want to smoke then make sure it’s the proper moisture level for smoking. This usually requires some dry time. How much dry time is up to you.
2) Insert the tobacco into the tobacco burning chamber. How exactly insertion is achieved is up to you.
3) Ignite tobacco once it’s in the tobacco burning chamber. How to do that is up to you.
4) Gently puff the mouthpiece of the pipe. How gently and how frequently is up to you.
5) When finished, knock out remnants from tobacco burning chamber then run pipe cleaners through the stem and stummel.
6) Repeat as necessary.
Best of luck!
Let us know how it goes.