I have the S-6 bypass oil filter on my 49 216. It does drain down to the oil pan but only about half it's content (maybe a 1/2 qrt). It takes 5 to 15 minutes or so for it to drain down after shutdown.
To keep from overfilling the oil pan too much on oil changes etc, what I do is fill the crankcase to the dip sticks full mark, then install the filter in the can and slowly fill it up. It takes about 1/2 qrt and button it up. Since it takes awhile for it to soak through and drain whatever amout it will, I generally wait 5 - 15 minutes before I check and run it.
It'll show over fill but not by much.

The C-6 filter can has an oil drain plug near the bottom so I pull the filter, remove the drain plug and give it a couple minutes to drain. Since I'm now in the habit of useing surgical gloves for messy jobs I then will take several papar towels and just reach in and manually wipe the can out clean. That is usually good enough to get it all out. When I pulled the head for rebuild I fully cleaned out the filter can w/kerosene and water and since then it hasn't collected too much sludge to where I couldn't towel it out.

Dave