Consider filling and lighting technique. The fill should be even and evenly compressed; it appears you're compacting the edge of the fill more than the center. A good fill (and a big help for a good smoke) is revealed when you brush the match (or whatever) across and around the top of the newly-filled bowl. The entire bowl should light completely and, more or less, uniformly. After it fluffs up and is given an initial tamp the relight should be complete across the top of the chamber. As you puff to light, dance your flame around the bowl and see if the entire top fires up. If yes, good fill; if no, pay more attention to the next fill. If your pipe gets swampy at the heel, make ure you start with a dry pipe. Use less tobacco for a while to improve your technique. Let a wad of loose tobacco dry out for 30-60 minutes pre-smoke if it's too moist.