Two times stand out lately - love to have a bowl with my morning coffee while it is quiet and I am alone - then when I get in from work and transition into family time
if you're considering a tasting journal you might try doing a blog - I do a few and one is dedicated to tasting and reminiscing about my pipe adventures - fun way to share
I don't know about breaking a pipe in - I can say every pipe I smoked was what it was from the beginning - there are some that cured and sweetened over time