Hi old red, and welcome to the forum. Glad you're here and that you're one of us. asking questions is exactly the way to go, because that's how we all learn. As to tamping, there are varying schools of thought, with some telling you to tamp firmly, others lightly, and so forth. I'll tell you how I do it and recommend you give my way a try. Pretty soon someone else will tell you his method, and I recommend you try that as well. Try different techniques, different tobaccos, different pipes, etc., because that's how expertise is built. Now here's the deep, dark secret of tamping: do it anytime you feel it needs it. Experience will tell you when to do it. Here's my take: when I feel that the cherry (the glowing portion of the tobacco that you can't see,) is giving signs of wanting to go out, I tamp down a bit. That sometimes encourages it to catch again and keep going, and other times just puts it out. Then relight, and keep going. Eventually your experience will tell you when to tamp. Just sip slowly. Your pipe should always be on the verge of just going out. That gives you the coolest and best flavored smoke.
Again--welcome to one of the worlds most enjoyable hobbies, and again, feel free to ask questions. You'll get a million answers, and these, coupled with your own experience will make you an expert.