1. Don’t start with super wet aromatics. They will bite you and potentially turn you off from pipe smoking altogether.
2. When the time comes for your first briar, invest in a quality, factory-made pipe as opposed to a basket pipe. Basket pipes can be poorly drilled and if you have no reference point for how a quality briar pipe smokes, you may think that you’re doing something wrong in your smoking, when it’s actually the pipe itself.
3. Straight pipes are easier to clean and drill correctly, so understand that if you start with a bent, there may be more issues with moisture.
4. Don’t worry one bit about dottle. I have at least some dottle in 99% of the bowls I smoke. As someone who smokes multiple bowls a day, I’d rather leave the last bit to dump out than risk lighting wet tobacco and blowing out my palette for the rest of the day.
5. If you’re a multi-bowl a day smoker, I would suggest at least 4 pipes. If you have 4, you can rotate between two different pipes a day while the other two rest so that each pipe gets a 24-hour break. I like to wait until there’s no more visible moisture in the bottom of the chamber before smoking the same pipe again that day, which usually takes 30 minutes to an hour or so. I would even recommend this for cobs but you could get away maybe with two cobs and just rotating daily between the two of them.