[Emjaysmash]

Pipe smoking is defintely an art form. While patience is needed at the beggining, the adage "practice makes perfect" still applies. The more practice you have, the easier it will be to judge how much tobacco you need, how tight to pack it, and how dry you like it.

Letting it dry out is a good start. take as much tobacco as you need to fill a bowl (probably a little more than that to be safe), and spread it out on a table to let sit.
Also, I've never had Capt. Black, but I can assume as it is a drug store tobacco and that it is a milder blend. Checking out your local B&M for their suggestions is a great idea.
Like all things, it takes time. I'm almost 2 years into pipe smoking and I've finally been able to find not only what tobacco I prefer, but how I like to smoke it and pack it. It's a journey, and while there are some ups and downs, eventually you will be rewarded! Dont give up!