So lemme help? The filler you want is actually air space. Generically speaking, imagine a plastic bowl upside down with a hole drilled into the top. Some holes very low on the sides might be helpful, but notches along the lip serve almost the same leaking purpose. Into the top hole you place a long plastic pvc pipe to refill water from above the soil surface. Mix the soil and compost and fill around and over the bowl and Voila'! A self watering container into which you may put a float with a flag to show you how low the water level is or you can make a dipstick to check it. Youtube has quite a few videos on "self watering" containers.
My advice on the pine cones is crunch them small. The soil will collapse over time as it is and pine cone will make it worse. Personally I would burn the pine and quench the hot fire to get charcoal out of it. That should not be used fresh, but because pine does not have lignin like hardwood does, it never makes humates the way ramial wood can. I really think the carbon is its main value long term, IF you tend to reuse soil like I would. Drainage is a good usage though, short term. Even dumped out into the lawn, biochar is helpful here where we have low organic matter levels in our clay soil.
Pine, wood or other not rotted organics have a tendency to be the main entree for a process requiring oxygen and nitrogen as it oxidizes and "composts" so in containers it is not the best idea to compost as you go. The plants will not be in a rich medium and you will spend more to fertilize both the plant and the bacteria and fungi breaking down the uncomposted materials.