Welcome,Slackerdriver
I also was a huge cigar fan-my wife cooperated and built a beautiful humidor in a piece of furniture which hold our tv and projector screen. She hates smoke, but the gesture was not lost on me!
Since getting back into pipes after so many years, the adjustment from cigar technique was substantial. I now never touch cigars and let my friends smoke them when they come over. (Ah, so sad)
Like any other skill, this will come in time. I frequently relight and don't care what so ever. The experience is so relaxing, unlike smoking a cigar. And, other than the cost of pipes and PAD (pipe acquisition disorder) the cost is substantially less!
Good luck
Allan