I don't even understand this whole "breaking in" concept. Pipes are constantly in a state of transformation, like a living thing... like a woman. You get a virgin pipe. You learn what makes it sing, and show it what you like; try a few different tobaccos in it, and see what she likes. Why start off wanting it to be used, enjoy that new briar flavor, bond with it, get it's DNA in your system. Clean it. Keep your cake beaten back to whatever you think you want. Then soon you'll want to deep clean it. But, if it starts getting to where you choose it less and les, ream her out and polish here, a make over, so to speak.
When does it smoke best? I enjoy it all. Give me a fresh virgin to enjoy, or a nice MILF pipe, a nice divorcée estate pipe. I could really care less about "breaking in." Just enjoy it. And, if you don't want to smoke for 45 minutes, just choose another method. But, I have had very few cigars that lasted less than 45 minutes. Personally, I want hours of smoking, hours upon hours.