A couple things to consider:
1. Most (not all, but most) don't worry about establishing cake in cobs pipes, it's more a practice for briars.
2. Sounds like your tobacco is too wet- try sitting it on a plate to dry under a lamp for an hour before smoking. You're in NY, so your relative humitdity should be high this time of year. You will generally get the most flavor out of tobacco that is between 55 and 60 rh when smoked (not to mention it burns better)
3. Pipes are more nuanced than cigars and the learning curve is a bit steeper. You want an initial char light (think toasting the foot of a stogie), then you want gentle draws while holding the flame over the charred tobacco. Over tamping can make it hard to stay lit as well. Let the weight of the tamp press the tobacco down rather than exerting force on it. A pipe should draw MUCH more loosely than most cigars if it is to burn properly.