jcdem', on keeping a pipe lit, dry the tobacco out a little, a few bowls at a time in a small container like an old cereal or crockery bowl, or pack the pipe and leave it overnight; do a "charring" light, an initial light, and when that goes out, tamp it gently to settle the tobacco in the bowl; tamp a little before each re-light to make sure the "fuel" is close enough together to burn evenly. The easiest blends to keep lit are some of the old pouch codger blends like Carter Hall and Prince Albert, and most people like them pretty well too. You'll find this gets easier as you go, and the ritual become muscle memory and doesn't seem as repetitious.