Thought I would post a quick update - as I don't know if I will be posting many more in this thread.
I have smoked quite a few bowls since starting, and am already getting better at slowing down and enjoying the experience. Of course, this will take years to truly master, but that I have gotten better already, has given me hope that pipe smoking may be a thing for me. It has even gotten to the point that I can take my Gurgle-king pipe (my first) and enjoy a bowl in it now (if I have a cleaner with me).
What's pulled me through, is noting that one can let a pipe go out as often as he wants and simply re-light. It's very empowering to note that re-lighting is part of the experience. As a cigar smoker - that was a huge stumbling block.
The other thing that's helped me along, is noting that you can jam a pipe cleaner through a pipe mid smoke if it's getting moist. That... well that has kept me from throwing out my gurgle pipe!
I guess most importantly, I have learnt that smoking a pipe is a personal experience and no two men smoke the same way. Its all about you and your pipe/tobacco. There is no pipe that everyone will like - nor is there a tobacco that everyone will like. Moreover, there is no single way to pack a pipe or single way to smoke it. Smoking a pipe really is all about what you make it. Which is somehow - very liberating.
I don't want to have a huge collection of pipes, but like every piper, I note every pipe has it's place and what's worse, it's hard not envisioning any pipe for sale in my mouth in a certain environment that would be perfect! Moreover, it's hard not to envision certain pipes smoking certain tobacco's better than others. My fears of collecting will probably be realized as I am seriously considering heading over to Chicago for the Pipe show there in May, but I'll try HARD to keep this aspect in check.
I am glad I have embarked on this journey. Last night, after the house had gone to sleep, I snuck out onto the patio and lit a bowl. The experience was almost zen-like. If I can replicate that once a week... once a month, it'll all have been worth it!
Thanks for reading - and thanks to all the Brothers on BOTL for the help and inputs. Some call it empowering - I call it enlightening.
Thanks again.