Thanks for all the advice guys. I'm stubborn and impatient so I decided to try the following:
1. Let the tobacco dry for a half hour before smoked (local blend called AUE TQ which I suspect is their version of 1Q
2. Packed the bowl much looser than ever before, probably close to half the normal amount I've been doing
3. Smoked a LOT slower
4. Had sweetened ice tea to drink with it
Had my best smoke yet! So flavorful, smooth and only had to re-light 2x. When I cleaned the pipe out (Brigham system pipe) the wooden filter was barely damp at the end, previously they have been soaked when I took them out to clean. Thanks for all the input, that was far and away the best smoke I've had yet.