How long and how tight?

Engine: 360 came with a front sump oil pan.

How long? With a center sump pan, the dip stick doesn't want to go in all the way. When it does, some of it is laying along the bottom of the pan. Is there a different stick needed. How long should the dip stick be from the bead that hits the tube top to the end be?

How tight? I want to reinstall the oil filter mount to the engine block. I can't find any thing about the correct torque in original or aftermarket service manuals. The "nipple" has a square drive inside.
I have seen threads about drilling extra holes in the plate for better flow. Would one between each existing hole be enough? (same dia.)
Thanks,
Mike