Flakes, even rubbed out ones, can be a tricky to keep lit just because of the density of the chunks. 8 hours of drying time is a pretty good amount. I'd suggest filling the pipe with less tobacco than you think you need. If the draw is too loose you can always tighten it up with the tamper, but you'll want to use that judiciously.

The volume of smoke, and the intensity of the flavors will be less than with a cigar, and trying to get big billows of smoke will burn your tongue. I know this isn't that helpful, but stick with it and eventually things will click. Using the frank method to fill my pipe helped me a lot in the beginning.